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Cataloged from PDF version of article. Thesis (Master's): Bilkent University, Graduate Program in Materials Science and Nanotechnology, İhsan Doğramacı Bilkent University, 2023. Includes bibliographical references (leaves 67-74). Nanomaterial-based therapeutic agents are drawing a lot of attention because numerous capabilities, including drugs, targeting groups, and photoactive units, can be combined on one platform to treat infectious diseases and cancer. In this regard, two different nanomaterials and their nanomedicine applications were re-ported. Firstly, red-emitting glycosylated conjugated oligomer (COL) nanopar-ticle was prepared and hybrid conjugation with gold nanoparticles was prepared by the nanoprecipitation method in order to examine photothermal applications. Due to their authentic electronic and optical characteristics, showing high sin-glet oxygen production ability, enabling control of the sizes of nanoparticles by acetyl groups in the side chains, enhancing their stability, and improving cell permeability via the hydrophobic effect they are promoting photosensitizers for photodynamic therapy. Secondly, chlorophyll, a natural photo absorbent, was ex-tracted from spinach leaves, and chlorophyll nanoparticles were prepared by nano-precipitation method because of their promoting properties which are high bio-compatibility, low production cost, and natural reductive chemical atmosphere, containing plenty of hydrogen atoms and being environmentally friendly. Then, hybrid conjugation with gold nanoparticles was prepared to investigate photother-mal therapy application. Both of the nanoparticles showed a high generation ability of reactive oxygen species (ROS) even at low light intensities and short exposure times which makes nanoparticles an ideal photosensitizer. From the antibacterial experiment, when Gram-negative (Escherichia coli, E. coli) bacteria were incubated with chlorophyll-based nanoparticles, a reduction up to 2.8-log and 2.33-log in colony-forming units (CFUs) was obtained under light irradiation for Chl-Au and Chl nanoparticles, respectively. Also, these nanoparticles showed minimal dark cytotoxicity (0.32-log and 0.15-log). On the other hand, conjugated oligomer-based nanoparticles precipitated in bacterial suspension and were un-able to pass across the cell wall of bacteria which was proved by SEM images and 4 mm and 5 mm inhibition zone were recorded for COL and COL-Au nanopar-ticles which are highly lower than ampicillin (7 mm). Along with these results, it is deduced that conjugated oligomer nanoparticles are not proper for antibac-terial photodynamic applications although the interaction between the bacterial cell wall and nanoparticle was promoted with gold conjugation. For anticancer photodynamic therapy applications, MCF-7 breast cancer cells were treated with these nanoparticles in the dark and under white light illumination for 20 min-utes, and the decline in cell viability was recorded at 50 %, 60 %, and 58 %, 72 %reduction for Chl, Chl-Au, and COL, Chl-Au nanoparticles, respectively. Also, they demonstrated dark cytotoxicity with the increment of concentration. Ad-ditionally, they also demonstrated the capacity for cellular imaging due to their inherent fluorescent properties, which might be used for image-guided PDT ap-plications. Along with this, the cytotoxicity results were supported by displaying the cellular uptake of nanoparticles and their surrounding the nucleus of breast cancer cells. by Ezgi Oduncu M.S.

Cataloged from PDF version of article. Thesis (Master's): Bilkent University, Graduate Program in Materials Science and Nanotechnology, İhsan Doğramacı Bilkent University, 2022. Includes bibliographical references (leaves 59-68). The intrinsic porosity and tunable morphology of Porous Organic Polymers (POPs), materials made from organic building blocks joined by strong covalent bonds, have become appealing in the context of electrochemical applications. In the first section of this thesis, a low-cost thiophene derivative and melamine were assembled into nitrogen and sulfur-enriched microporous organic polymer (MOP) using a pyrolysis-free one-pot Schiff-base type polycondensation reaction. The synthesized polymer is characterized by FT-IR, SEM, TEM, BET, XRD, XPS, TGA and UV-VIS. With 195.731 m2 g–1 surface area and 0.047 cm3 g–1 pore volume, the as-synthesized MOP has a cotton-like morphology and a micropore-dominated pore size distribution. After encapsulating it with a nickel co-catalyst, we showed that the obtained framework (MOP) could be used as an efficient catalyst for hydrogen evolution reaction (HER) in an alkaline electrolyte with the optimum composite (Ni2@MOP) exhibiting a remarkable onset overpotential of -66 mV. Furthermore, the optimum electrocatalyst showed good stability, delivering 90.84% faradaic efficiency (FE) after a 3.5 h chronoamperometry experiment. In the second section, the synthesized porous organic polymer and CB[6]-porphyrin covalent organic framework were investigated for potential use as electrode materials for supercapacitors. by Arma Musa Yau M.S.

Cataloged from PDF version of article. Thesis (Master's): Bilkent University, Department of Materials Science and Nanotechnology, İhsan Doğramacı Bilkent University, 2021. Includes bibliographical references (pages 73-83). Environmental problems and climate changes have increased the importance of studies on the development of sustainable and clean energy methods that can be an alternative to energy production technologies using fossil fuels in recent years. Green hydrogen is environmentally friendly and a high-capacity energy carrier, as it does not cause any toxic by-products during its production. For this reason, attempts are being made to increase the efficiency of green hydrogen produced from water splitting. Development of the catalytic activities and stability of electrocatalysts has gained great importance in order to increase the performance of the hydrogen evolution reaction (HER). This study examines the effect of Ni/NiO-reduced graphene oxide catalysts fabricated in the form of heterostructured fibers by electrospinning on their intrinsic and extrinsic activities and their performance for HER. In order to examine the stability, activity and kinetics of the synthesized electrocatalyst, studies such as linear sweep voltammetry (LSV), electrochemical impedance spectroscopy (EIS), chronoamperometry (CA), were carried out and Tafel curves were interpreted. It has been observed that the optimal electrocatalyst exhibits outstanding electrocatalytic performance with an over potential of -212 mV at 10 mA cm-2, and a Tafel slope of 90.6 mV dec-1 in alkaline electrolyte. Morphological and structural characterizations of electrocatalysts were investigated using X-ray diffraction (XRD), fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS), Raman spectroscopy, and transmission electron microscopy (TEM) methods. by Elif Begüm Yılmaz M.S.

Cataloged from PDF version of article. Thesis (Master's): Bilkent University, Department of Chemistry, İhsan Doğramacı Bilkent University, 2021. Includes bibliographical references. (leaves 63-70). Nanomaterial-based compounds are attracting a lot of interest because many functionalities such as photoactive units, drugs and targeting groups can be combined on one platform to fight against infectious diseases and cancer. Recently, conjugated polymer-based nanomaterials have proven to be effective photosensitizers for antibacterial and photodynamic cancer therapies owing to their unique electronic and optical properties, including high singlet oxygen generation capacity, strong light-harvesting ability and its tunable optical spectrum. In this study, novel cross-linked conjugated polymer nanoparticles-based photosensitizers namely conjugated polymer-porphyrin nanoparticles (CPPN) and cross-linked conjugated polymer nanoparticles (PCP) were synthesized. The nanoparticles were prepared via nanoprecipitation using cucurbit[6]uril-(CB6)-catalyzed azide-alkyne cycloaddition (CB6-AAC) reaction. Conjugated polymer-porphyrin nanoparticles (CPPN) are advantageous than micelles incorporating porphyrin systems. For micelles containing porphyrin systems, the phototherapy effect of the porphyrin can only be seen after the porphyrin is released by conditions such as a change in pH, which is not the case for conjugated polymer-porphyrin nanoparticles (CPPN). The nanoparticles demonstrated high reactive oxygen species (ROS) generation efficiency which is evident in the antibacterial and anticancer photodynamic therapy (PDT) experiments. From the antibacterial photodynamic therapy experiment, when Gram-negative (Escherichia coli, E. coli) and Gram-positive (Bacillus subtilis, B. Subtilis and Staphylococcus aureus, S. aureus) bacteria were incubated with CPPN (20 µg/mL) and irradiated with white light (22 mW/cm2) for 10 min, more than 3.5-log reduction in colony-forming units (CFUs) was recorded for CPPN. Furthermore, when E. coli and B. subtilis were treated with PCP (24 µg/mL) and illuminated with light, about 3-log killing efficiency was recorded. However, in the dark, the nanoparticles demonstrated minimal dark cytotoxicity against the model bacteria. In addition, the anticancer photodynamic effect of CPPN and PCP on MCF-7 breast cancer cells was investigated. When MCF-7 breast cancer cells were treated with PCP in the dark and under light irradiation, almost all cells were alive for both cases. It may be that PCP could not generate enough reactive oxygen species to kill the cells. When MCF-7 breast cancer cells were treated with CPPN in the dark, the cell viability was 96% and upon irradiation with light for 20 minutes, the cell viability decreased to about 4%. Moreover, conjugated polymer-porphyrin-gold nanoparticles (CPPN-Au) and cross-linked conjugated polymer-gold nanoparticles (PCP-Au) nanoparticles were prepared, but due to the instability of the nanoparticles, they could not be used in phototherapy. by Ishmeal Kwaku Duah M.S.

Cataloged from PDF version of article. Thesis (M.S.): Bilkent University, Department of Materials Science and Nanotechnology, İhsan Doğramacı Bilkent University, 2021. Includes bibliographical references (leaves 64-73). There is great apprehension about consumption of fossil fuels as well as the corresponding environmental issues which has evoked supreme efforts worldwide to develop clean and sustainable energy sources. Electrocatalytic water splitting producing both hydrogen and oxygen gas has shown considerable potential for energy conversion as hydrogen can meet the requirements for future energy demands. Hence it is of utmost importance to introduce novel electrocatalysts to overcome energy barriers for hydrogen evolution reaction (HER) and oxygen evolution reaction (OER). Here this thesis highlights the synthesis and characterization of a novel supramolecular assembly of cucurbit[6]uril and porphyrin and also examines its electrocatalytic activity toward both HER and OER. Electrochemical studies such as linear sweep voltammetry, chronoamperometry, chronopotentiometry, electrochemical impedance spectroscopy were performed to investigate the activity of the catalyst. The structural and morphological properties of sample were also studied using scanning electron microscopy (SEM), X-ray diffraction analysis (XRD), X-ray photoelectron spectroscopy (XPS) and Fourier-transform infrared spectroscopy (FT-IR). It was observed that the catalyst was able to show excellent electrocatalytic activity with onset potentials of -0.25 V (for HER) and 1.6 V (for OER) while producing 18.7 and 14.92 mmol.gr-1.hr-1 hydrogen and oxygen gas with faradaic efficiencies of 85% and 99%, respectively. by Yasaman Sheidaei M.S.

Cataloged from PDF version of article. Thesis (M.S.): Bilkent University, Department of Materials Science and Nanotechnology, İhsan Doğramacı Bilkent University, 2020. Includes bibliographical references (leaves 75-88). The ever-increasing demands for energy have encouraged an enormous consumption of fossil fuels worldwide. This has presented major concerns due to their limited resources and serious environmental issues. Therefore, the search for an alternative clean energy fuel has been intensively under study. In the past decade, hydrogen has attracted great attention as a promising fuel for the future. Hydrogen is an eco-friendly fuel that is readily abundant, highly efficient and clean since water is its only combustion product. Herein, this thesis highlights the synthesis and characterization of a novel supramolecular assembly based on cucurbit [8] uril -porphyrin functionalized on electrochemically reduced graphene oxide sheets for application in electrochemical hydrogen evolution. The study conveys optimization procedures for choosing the best catalytic system. Electrochemical analysis including potentiometry, cyclic voltammetry, chronoamperometry and electrochemical impedance spectroscopy were used to evaluate activity and stability. Characterization techniques were also performed to analyze the morphology and chemical structures of composites. Electrochemical studies demonstrated that ERGO: Ni-P composite (which comprises of a layer of graphene oxide drop-casted on FTO followed by a layer of nickel CB[8]-porphyrin) can serve as an excellent electrocatalyst for hydrogen evolution in alkaline medium. The composite exhibited high activity (onset potentialv -20 mV, 56.9 mmol h−1g −1 hydrogen, faradaic efficiency of 93% ), remarkable rate of charge transfer (Rct v 210 Ω), large electrochemical surface area (Cdl v1.67 mFcm−2 ) and significant stability without requiring additional noble metals. by Bouthaina Aoudi M.S.

Cataloged from PDF version of article. Thesis (M.S.): Bilkent University, Department of Materials Science and Nanotechnology, İhsan Doğramacı Bilkent University, 2020. Includes bibliographical references (leaves 101-123). The supramolecular chemistry of cucurbiturils (CBs) has been rapidly advancing to span wide range of nanomedicine applications including but not limited to pharmaceutical drug formulation and delivery, bio/medical imaging and sensing, cancer therapy, tissue engineering, development of antibacterial/antiviral agents and protein modification. Owing to unique recognition properties and low cytotoxicity, the supramolecular assemblies of CBs are particular promises for biomedicine tasks. Inspired by these developments, three multifunctional supramolecular constructs of CBs containing photoactive conjugated compounds were prepared to be utilized in nanomedicine applications covering antimicrobial and anticancer photodynamic therapy (PDT), combined PDT and photothermal therapy (PTT) for the inactivation of bacteria, drug delivery and cellular imaging. A stable rotaxane, namely [5]-rotaxane, based on photoactive alkynesubstituted porphyrin and azide-substituted stopper group was synthesized through 1,3-dipolar cycloaddition reaction. Herein, cucurbit[6]uril (CB6) acts as both macrocycle and catalysis for the reaction and encapsulates formed triazole ring inside its cavity. [5]-rotaxane was further investigated and results revealed that it has ability to generate reactive oxygen species (ROS) including singlet oxygens in high yield even under quite low fluence of light and short exposure time and this, in turn, renders it ideal photosensitizer which remains stable at physiological pH (7.4) for prolonged times. By taking the advantages of aforementioned properties, [5]-rotaxane was employed as a broad-spectrum antibacterial agent against Gram-negative and Gram-positive bacteria as well as anticancer agent against human breast cancer cell line (MCF-7) via visible-light-induced generation of ROS. [5]-rotaxane possess negligible dark cytotoxicity upon complexation with CB6 and it can afford efficacious PDT of cancer and infectious diseases caused by bacteria. Another multifunctional photoactive supramolecular assembly was built through covalently binding of four cucurbit[7]uril (CB7) molecules, functioning as receptor, to a tetraphenyl porphyrin core using suitable linkers. In addition to its light-promoted antibacterial property, here, main objective was to combine chemo- and photodynamic cancer therapy which makes this study novel. Presence of CB7, enables host-guest interactions with anticancer drug, doxorubicin hydrochloride (DOX), and therefore this system was used to carry drug molecules achieving synergistic PDT and chemotherapy. Finally, CB7-capped hybrid nanoparticles (NPs) made up of red-emitting conjugated oligomer (COL) and gold nanoparticles (Au-NPs) were obtained through one-pot synthetic method. These hybrid NPs were found to own high photostability, thermal reversibility and high ROS generation capacity. Benefitting from these properties, combined photodynamic and photothermal killing efficiency of NPs towards Gram-positive and Gram-negative bacteria was verified. Additionally, cellular imaging capability of them was shown owing to their inherently fluorescent characteristics and this feature could be utilized for image-guided PDT applications. by Melis Özkan M.S.

E. coli bakterisindeki çoklu ilaç direnci (MDR) insanlarda olduğu kadar hayvanlarda da giderek yaygınlaşan endişe verici bir sorun haline gelmiştir. Bu nedenle geleneksel antibiyotiklere alternatif etkili ilaçlar geliştirmek zorunlu hale gelmiştir. Bakterilerin geleneksel antiboyatiklere karşı direnç gösterdiği durumlarda fotodinamik tedaviden (PDT) yararlanma düşüncesi bakterileri yok etmek için bir çözümdür. PDT bu durumlarda bir seçenek olmasına rağmen, bakterileri yok etme verimliliği çoğu zaman yeterli değildir ve bir takım iyileştirmeler yapmak gerekmektedir. Metalle artırılmış singlet oksijen (ME1O2) üretimi PDT ile E. coli bakterisini öldürme verimliliğini artırma yollarından biridir. Bu tür yapılar, polimerlerin (kabuk) esnek ve ayarlanabilir özelliklerini plasmonik metallerin (çekirdek) optik, elektronik ve fotofiziksel özellikleriyle bir araya getirebilir. Bu çalışmada, altını çekirdek olarak kullanıp konjuge oligomeri kabuk olarak kullanarak, yüksek singlet oksijen üretim verimine sahip olan ve E. coli bakterisini öldürme verimi artırılmış hibrit çekirdek-kabuk nanoparçacıkları sentezlenmiştir. Bu yapıda kabuk, altın iyonlarının spontane indirgenerek altın nanoparçacıkları oluşturmasından ve agregasyondan korunmasından sorumludur. Detaylı araştırma ve iyileştirmelerle, hibrit çekirdek-kabuk nanoparçacıkları, ME1O2'nin de yardımıyla, E. Coli öldürme verimini %40 artırmıştır. Multidrug resistance (MDR) in Escherichia coli (E. coli) has become a worrying issue that is not only increasingly observed in humans but also is widespread in veterinary medicine worldwide. Therefore, developing new and effective alternatives to conventional antibiotics has become an imperative need. The idea of using photodynamic therapy (PDT) for bacterial eradication is a solution for the cases that the bacteria are resisting to conventional antibiotics. Although in these cases, PDT can be an option, PDT-killing efficiency might still not be sufficient, and some enhancements are necessary. Metal-enhanced singlet oxygen generation (ME1O2) is one of the ways to enhance the PDT-killing efficiency of the E. coli. Hybrid core-shell structures can serve conveniently for this purpose. These structures can combine the flexible and tailorable features of polymers (shell) with the photophysical properties of plasmonic metals (core). In this work, using gold as a core and conjugated oligomer as a shell produced a novel hybrid core-shell nanoparticles which can enhance the singlet oxygen generation capacity and subsequently, improve the PDT-killing efficiency of the E. coli. In this structure, the shell is responsible for the spontaneous reduction of gold ions, forming gold nanoparticles and protecting them from the aggregation. With further investigation and optimization, the hybrid core-shell nanoparticles with the help of ME1O2 successfully improved the killing efficiency of E. coli bacteria by 40%. 137

Kükürbitüril tabanlı işlevsel malzemelerin hazırlanması ve biyomedikalden optoelektroniğe uzanan farklı uygulamalarda kullanımı son yıllarda yoğun şekilde çalışılmaktadır. Kükürbitürillerin konjuge -bağı içeren fotoaktif maddelerle kovalent olmayan etkileşimler aracılığıyla oluşturdukları supramoleküler yapılar, ağlar ve nanomalzemeler de araştırılmakta ve teranostik, görüntüleme, moleküler algılama ve kataliz alanlarındaki olası uygulamaları gösterilmektedir. Fakat, kükürbitüril tabanlı bu mimarilerde, kükürbitüril doğrudan kovalent bağlarla kromofora bağlanmadığından, bir moleküler reseptör olarak işlev gösterememektedir. Bu çalışmanın temel motivasyonu ise kükürbitürilin kovalent bağlarla porfirine, konjuge oligomere ve polimere bağlandığı çok işlevli platformların ve nanoyapıların sentezidir.Fotoaktif mannozlanmış porfirin ve monoproparjiloksikükürbit[7]üril tabanlı yeni bir çok işlevli porfirin-kükürbitüril konjugesi sentezlendi. Azido-fonksiyonlu tetrafenilporfirin (TPP) yapı taşı olarak kullanıldı. Öncelikle, TPP, bakır katalizörlü azit-alkin siklokatılma (CuAAC) tepkimesi ile mannozlandı. Sonrasında, monoproparjiloksikükürbit[7]üril, ikinci bir CuAAC tepkimesi ile mannozlu TPP'ye kovalent bağla bağlandı. Elde edilen supramoleküler platformun singlet oksijen üretme verimliliği ölçüldü ve işlevselleştirilmemiş TPP'ninkinden önemli derecede yüksek olduğu kanıtlandı. Supramoleküler platformun yapısında bulunan kükürbit[7]ürilin konak molekül olarak elverişliliğinin kanıtlanması amacıyla uygun bir konuk molekül, bisimidazolyum, kullanarak 1H NMR deneyleri yapıldı. Bisimidazolyumun kükürbit[7]üril ile kuşatan kompleks oluşturduğu gözlemlendi ki bu sentezlenen supramoleküler platformun, fotodinamik tedavinin yanında ilaç taşıyıcı olarak da kullanılma potansiyelini gösteren umut verici bir sonuçtur.Uygun şekilde fonksiyonel gruplarla donatılmış monomerler arasında Pd katalizli çapraz eşleşme reaksiyonları ile farklı yapıdaki konjuge oligomer ve polimerler sentezlendi ve karakterize edildi. Bu konjuge malzemelerin kovalent bağlanmış kükürbitüril ile oluşturdukları platformlar ve nanoyapılar çalışıldı. Bir konjuge oligomer, OFVBt-N3, ve bir disülfit bağı içeren çapraz bağlayıcı kullanarak THF içinde ultrason yardımlı bakırsız çıt-çıt tepkimesi ile redoks duyarlı konjuge oligomer nanoparçacıkları (CONs) sentezlendi. Ortalama 50 nm boyutlu ve küresel yapıdaki bu nanoparçacıklar suda dağıldıktan sonra da boyut (≈60 nm) ve kararlılıklarını korudular. Nanoparçacıkların sulu ortamda, glutatiyon (GSH) varlığındaki davranışları çalışıldı ve kanser hücrelerinde aşırı üretilen bir biyomolekül ve etkili bir S-S bağı kırıcısı olan GSH tarafından nanoparçacıkların bozulduğu görüldü. Dolayısıyla, bu nanoparçacıklar bir kanser ilacıyla yüklendiğinde, ilacın kanser hücrelerine hedeflenmiş iletimi, artmış geçirgenlik ve alıkonma (EPR) etkisi ve S-S bağının GSH tarafından kırılmasının işbirliği ile başarılabilir. Preparation of cucurbituril based functional materials and their use in various applications ranging from biomedicine to optoelectronics have been studied intensely over the last decade. Supramolecular assemblies, networks and nanostructures constructed through noncovalent interactions of cucurbiturils with -conjugated, photoactive compounds have also been investigated and potential applications in the areas of theranostics, imaging, sensing and catalysis have been shown. In these cucurbituril based architectures, however, cucurbituril is disabled to act as a molecular receptor since they do not involve the covalent conjugation of cucurbituril directly to chromophore. The main motivation of this study is to synthesize multifunctional assemblies and nanostructures in which cucurbituril is covalently attached to various conjugated compounds including porphyrin, conjugated oligomers and polymers.A new multifunctional porphyrin-cucurbituril conjugate based on a photoactive mannosylated porphyrin and monoporpargyloxycucurbit[7]uril was synthesized. Azido-functionalized tetraphenylporphyrin (TPP) was used as a building block. TPP was first mannosylated by copper-catalyzed azide-alkyne cycloaddition (CuAAC), then a monoporpargyloxycucurbit[7]uril was covalently attached to the mannosylated TPP with a second CuAAC reaction. Singlet oxygen generation efficiency of the supramolecular assembly was measured and found to be significantly higher than that of unfunctionalized TPP. 1H NMR experiments were performed using a suitable guest, bisimidazolium, to prove the availability of CB7 in the assembly as a host. Bisimidazolium guest was observed to form inclusion complex with CB7, which is a promising result for the potential use of this supramolecular assembly as a drug carrier in conjunction with photodynamic therapy.Conjugated oligomers and polymers were synthesized from suitably-functionalized monomers via Pd-catalyzed cross-coupling reactions and their characterizations were performed. Their assemblies and nanostructures with covalently attached functionalized cucurbiturils were investigated. Redox sensitive crosslinked conjugated oligomer nanoparticles (CONs) were synthesized from a conjugated oligomer, OFVBt-N3 and a disulfide bond-containing crosslinker via ultrasound-assisted copper-free click reaction in THF. These spherical and approximately 50 nm-sized CONs preserved their stability and size (≈60 nm) after dispersing them in water. The behavior of the CONs in the presence of glutathione (GSH) was studied in aqueous medium. It was observed that the CONs are rapidly disrupted by GSH, which is an effective S-S bond cleaving biomolecule that is overexpressed in cancer cells. These results imply that when nanoparticles are loaded with an anticancer drug, targeted delivery of the drug to cancer cells can be achieved by cooperative action of enhanced permeability and retention (EPR) effect and S-S bond cleavage by GSH. 167

Bu çalışma polimerlerle kaplanmış demir oksit nanoparçacıklarının potansiyel invivo ve in vitro görüntüleme yöntemlerinde kullanılmasını amaçlar. Konjugepolimerle hibritleştirilerek sentezlenen suya karışabilen, stabil süper-paramanyetikdemir oksit nanoparçacıklarının (SPIONs) sentezi üç ayrı bölgede ışıyan mavi,yeşil ve kırmızı polimerlerle yapıldı. Manyetik duyarlılığından dolayı T2 tipikontrast malzemesi olan SPION'ların bir diğer özelliği karaciğer, kemik iliği vedalaktaki kuppfer hücreleri tarafından özel içeri alınış biçimidir. Demir oksitnanoparçacıklarının çekirdek olarak kullanılması ve kaplanması kandaki dolaşımsüresini arttırmak, kanda topaklanmasını azaltmak ve farmokokinetik etkisinigeliştirmek üzere yapılmıştır.Bu çalışmada kullanılan konjuge polimerler çapraz bağlanabilir fonksiyonelgruplar elde etmek amacıyla alil ilave gruplarıyla modifiye edildi. Polimerzincirlerinin kararlılık kazanması için etilin grupları UV ışığı altında [2+2] siklokatılım reaksiyonuyla çarpa bağlandı. Çapraz bağlanma sadece kararlılıksunmakla kalmayıp, aynı zamanda SPION'ların polimer matrisinden biyolojikmedyaya erken kaçışını da önleyebilecek.Bu amaçla kullanılan üç polimer şunlardı, poli[(9,9-dihekzil fulorenil-2,7-diyil)-co-(9,9-bis {3-dialil}fulorenil-2,7-diyil)] (PB), poli[(9,9-bis ({3-dialil}fulorenil-2,7-diyil)-co-(benzotiyadiyazol)] (PG) and poli[3-{(aliloksi)etil} (tiyofen 2,5-vidiyil)-co-(5,5'-{2,2'}-bitiyofen)] (P2). Bu polimerlerin SPIONs içeren veiçermeyen nanoparçacıkları sentezlendi. Optik ve Morfolojik karakterizasyonlarıise sırasıyla Dinamik Işık Saçılımı (DLS) ölçümleri, Taramalı ElektronMikroskobu (SEM), Geçirimli Elektron Mikroskobu (TEM), UV-Vis veFlüoresans Spektroskopi yöntemleriyle incelenmiştir. This study focuses on the synthesis and characterizations of conjugated polymercoated super-paramagnetic iron oxide nanoparticles for their potential uses in vivoand in vitro imaging. Water dispersible, stable super-paramagnetic iron oxide(SPIO) hybridized conjugated polymer nanoparticles are synthesized with threedifferent types of conjugated polymers emitting in the region of blue, green andred. SPION, which is a T2 contrast agent due to its magnetic susceptibility, istaken into consideration because of its unique uptake mechanism by the Kupffercells in the liver, spleen or bone marrow.[1] The core iron oxide nanoparticles arecoated to increase blood circulation time, reduce the agglomeration of them andimprove pharmacokinetic effect.2Conjugated polymers utilized in this work were modified with allyl pendantgroups in order to obtain cross linkable moieties. Polymer chains were crosslinkedvia [2+2] cycloaddition of ethylene units under UV light to conferstability .Cross-linking would not only confer stability to these hybridnanoparticles but it can also help preventing the early leakage of SPIONs from thepolymer matrix in the biological media.For this purpose, three polymers used in this study, which were poly[(9,9-bis{3-dihexyl}flourenyl-2,7-diyl)-co-(9,9-bis{3-diallyl}fluorenyl-2,7-diyl)] (PB),Poly[(9,9-bis ({3-diallyl}flourenyl-2,7-diyl)-co-(benzothiodiazole)] (PG) and ivpoly[3-{(allyloxy)ethyl} (thiophene 2,5-diyl)-co-(5,5'-{2,2'}-bithiophene)] (P2).Nanoparticles of these polymers with and without SPIONs were synthesized.Optical and morphological characterizations were investigated via DLS, SEM,TEM, UV-Vis and Fluorescence spectroscopy. 104

Bu çalışmanın ilk bölümünde, porfirin-tiyofen tabanlı monomerler, oligomerler ve polimerler, foto dinamik terapi uygulaması için sentezlendi. Bir molekülün iyi bir foto uyarıcı olabilmesi için suda çözünürlüğünün iyi olması ve singlet oksijen üretme veriminin yüksek olup, tümörlü hücreye zarar vermesi gibi koşulları sağlaması gerekmektedir. Bu amaçla, oligomer ve polimer elde etmek için, tiyofin ile eşleşme reaksiyonundan önce, suda çözünür yan gruplar porfirin molekülüne takıldı. Porfirin tabanlı oligomer ve polimerin, tiyofende bulunan sülfür atomunun ağır atom etkisi yaratıp, porfirinin singlet elektronik durumundan triplete geçişini kolaylaştıracağı ve dolayısı ile reaktif oksijen radikallerinin oluşum verimini de yükselteceği bilinmektedir. Sonuç olarak, polimerin reaktif oksijen radikallerinin oluşum verimi, oligomer ve monomerin reaktif oksijen radikallerinin oluşumunundan daha fazla olduğu gözlenildi.Çalışmanın ikinci kısmında ise, kükürbitürilin iyonik konjuge polimerlerin uzerine fotofiziksel, elektrokimyasal ve termal özellikleri etkisi incenlendi.Konjuge polimerlerin ilginç optik özelliklerinden dolayı, bu polimerler ışık yayıcı diyotların alanında kullanılmaktadır. Fakat, konjuge polimerin üst üste binme yapısından dolayı flüoresans verimi düşer bu da foto uygulamarını sınırlandırır. Eğer polimerler zincirleriviarasında etkileşimler azatılırsa veya polimer omurgaları bazı yollarla izole edilirse, polimerlerin emisyon verimliliği arttırılabilir.Bu amaçla, iki farklı yeşil ışık yayan fluoren-tiyofen tabanlı polimerler (29 ve 33) ve bunların kükürbitüril tabanlı polirotaksanlar (30 ve 34) Suzuki eşleşme yoluyla sentezlendi. Hem polirotaksan 30 hem de polirotaksan 34'te flüoresans verimi artışı gözlendi. Polimer (29), polimer (33), polirotaksan (30) ve polirotaksan (34) 0.1, 0.35, 0.46 ve 0.55 sırasıyla flüoresans kuantum verimine sahipler.Bu malzemelerin optik ve elektrokimyasal özellikleri daha da incelemek için çok tabakalı beyaz polimer ışık yayan diyotlarda (PLEDs) kullanıldı.Sentezlenen malzemelerin yapılarını tayin etmek için, nükleer manyetik resonans spektrometresi (NMR), kütle spektrometresi, UV-Vis, Flüoresan, zaman ayrımlı floresans spektroskopisi, kızıl ötesi (FT-IR) spektrometresi, elemental analiz, jel geçirgenlik kromatografisi (GPC), termogravimetrik analiz (TGA) ve döngüsel voltametri yöntemlerinden yararlanıldı. In the first part of this study, porphyrin-thiophene monomers, oligomers and polymer are synthesized for photodynamic therapy application. Water solubility and the ability of a photosensitizer to generate singlet oxygen for tumor destruction are important conditions for ideal photosensitizer in photodynamic therapy application. For this purpose, water soluble pendent groups are attached to the porphyrin monomers before coupling with thiophene monomer to form oligomers and polymer. The presence of sulfur atom in thiophene facilitates intersystem crossing due to spin-orbit coupling and thus will increase singlet oxygen generation. Consequently, the ability of singlet oxygen generation of the polymer is found to be higher than oligomers followed by monomers.In the second part of the thesis, the effects of cucurbit[n]uril on photophysical, electrochemical and thermal properties of ionic conjugated polymers in water are described.Conjugated polymers are well known for their interesting optical properties and are used in the area of light emitting diodes. However, their stacking nature reduces their fluorescent quantum yields and thus limits their further applications. If the interactions among the polymers chains are reduced or the polymer backbones are insulated in some means, the emission efficiency of the polymers could be enhanced.For this purpose, two different green emitting fluorene-thiophene based polymers (29 and 33) and their cucurbituril based polyrotaxanes counterparts (30 and 34) are synthesized through Suzuki Coupling. In both polyrotaxane 30 and 34, enhancement in optical properties wasobserved showing fluorescent quantum yields of 0.46 and 0.55 in water respectively comparing to polymers 29 and 33 which has only 0.10 and 0.35 in water respectively.Their optical and electroluminescent properties were further utilized by fabricating devices as multilayer white polymer light emitting diodes (PLEDs).The synthesized molecules are characterized by 1H-NMR, 13C-NMR, ESI mass spectrometry, UV-VIS, photoluminescence, time resolved fluorescence spectroscopy, FT-IR, elemental analysis gel permeation chromatography, size exclusion chromatography, thermogravimetric analysis and cyclic voltammetry. 153

Ankara : Materials Science and Nanotechnology Program of The Graduate School of Engineering and Science of Bilkent University, 2014. Thesis (M.S.) -- Bilkent University, 2014. Includes bibliographical references leaves 84-86. In this study, green and near-infrared emitting stimuli responsive conjugated polymer nanoparticles that can be utilized simultaneously for chemotherapeutic drug delivery and bioimaging were synthesized. The nanoparticles are sensitive to low pH values of tumor microenvironment or elevated redox potential of some tumor types. These theranostic platforms could be used for in-vivo imaging and perform controlled-drug release triggered by an appropriate stimulus. For this purpose, green emitting polymer with fluorene and benzothiadiazole alternating units in the backbone and a conjugated polymer emitting in the red-NIR region based on thiophene and benzothiadiazole alternating units in the backbone were synthesized and characterized. Nanoparticles of these polymers (CPNs) were prepared by a simple method called nanoprecipitation where hydrophobic polymer chains collapse onto each other in aqueous media, trapping any other hydrophobic drug molecules (anticancer agent camptothecin in our case) in the environment inside the polymer matrix. Nanoprecipitation process was optimized for each polymer to obtain maximum drug encapsulation rate and a narrow nanoparticle size distribution under 100 nm. Resulting CPNs were stable for a long time in PBS buffer, water, bovine serum albumin and human plasma. SEM images showed spherical particles with a narrow diameter distribution. In vitro drug release studies, pH responsive CPNs showed faster drug release in more acidic media. Redox sensitive red polymer on the other hand showed a cleavage of disulfide bond in its structure in the presence of stimulus. To evaluate the cytotoxicity of drug loaded and blank CPNs RT-CES (real-time cell electronic sensing) assays with HuH-7 cell line have been carried out. While blank CPNs show an insignificant temporary cytotoxicity, camptothecin loaded nanoparticles match or outperform the growth inhibition effect of free camptothecin. Fluorescence microscopy images of HuH-7 cells incubated with CPNs clearly show CPNs that are internalized by cells. In conclusion, it was demonstrated that conjugated polymers could be used to fabricate theranostic platforms without the need for an additional imaging agent and their structures can be engineered to obtain stimuli responsive smart drug delivery systems. These results promise simple and easily fabricated smart systems that can selectively carry anticancer agents to tumors while enabling monitoring of drug distribution and inexpensive tumor imaging without using any harmful rays on the highly energetic side of the electromagnetic spectrum. Özgün, Alp M.S.

Ankara : The Department of Chemistry and the Graduate School of Engineering and Science of Bilkent University, 2011. Thesis (Master's) -- Bilkent University, 2011. Includes bibliographical references leaves 68-74. The general objective of this thesis is to explore the ability of cucurbit[n]uril (CB[n]) (n= 6,7,8) homologues to form nano-structured supramolecular assemblies with various organic guests through self-sorting, self-assembly and recognition. In the first part of the thesis, the selectivity and recognition properties of CB[n] homologues towards a ditopic guest have been investigated. The guest was synthesized through Cu(I)-catalyzed click reaction between the salts of N,N'-bis-(2- azido-ethyl)-dodecane-1,12-diamine and propargylamine and contain two chemically and geometrically distinct recognition sites, namely, a flexible and hydrophobic dodecyl spacer and a five-membered triazole ring terminated with ammonium ions. Complex formation between the guest and CB[6], CB[7] and CB[8] in the ratios of 1:2, 1:1 and 1:1, respectively, was confirmed by 1H NMR spectroscopy and mass spectrometry. It was also revealed that CB[n] homologues have ability to self-sort and recognise the guests according to their chemical nature, size and shape. Kinetic formation of a hetero[4]pseudorotaxane via sequence-specific self-sorting was confirmed and controlled by the order of the addition. In the second part, the effect of CB[n] homologues on the dissolution and the photophysical properties of non-ionic conjugated polymers in water were investigated. A fluorene-based polymer, namely, poly[9,9-bis{6(N,N dimethylamino)hexyl}fluorene-co-2,5-thienylene (PFT) was synthesized via Suzuki coupling and characterization was performed by spectroscopic techniques including 1D and 2D NMR(Nuclear Magnetic Resonans), UV–vis, fluorescent spectroscopy, and matrix-assisted laser desorption mass spectrometry (MALDI-MS)(Matrix Assisted Laser Desorption/Ionization Mass Spectroscopy ). The interaction of CB[6], CB[7] and CB[8] with PFT have been investigated and it was observed that only CB[8] among other CB homologues forms a water-soluble inclusion complex with PFT. Furthermore, upon complex formation a considerable enhancement in the fluorescent quantum yield of PFT in water was observed. The structure of resulting PFT@CB[8] complex was characterized through 1H-NMR and selective 1DNOESY(The Nuclear Overhauser Enhancement Spectroscopy) and further investigated by imaging techniques (e.g. AFM(Atomic Force Microscopy), SEM(Scanning Electron Microscopy), TEM(Transmission Electron Microscopy) and fluorescent optical microscopy) to reveal the morphology. The results suggested that through CB[8]-assisted self-assembly of PFT polymer chains vesicle-like nanostructures formed. The sizes of nanostructures were also determined using dynamic light scattering (DLS(Dynamic Light Scattering)) measurements. Artar, Müge M.S.

ÖZETPOLİFLOREN TÜREVLERİ ve POLİPİROL TABANLI KONJUGE POLİMERLERÜNSAL KOLDEMİRKimya Bölümü Yüksek Lisans TeziTez Yöneticisi: Doç. Dr. Dönüş TuncelTemmuz 2007Bu tezde, ışık yayan diyotlarda kullanılması amacıyla Suzuki Birleştirme yöntemi ile birseri polifloren tabanlı kopolimerler hazırlanmıştır. Polifloren tabanlı polimerler farklıbant aralığına sahip monomerlerden sentezlenmiştir. Bu polimerler FT-IR, UV-VIS,Floresans ve 1H, 13C NMR spektroskopi yöntemleri ile analiz ve karakterize edilmiştir.Konjüge polimerler doğal olarak yük taşıyabildiklerinden çok ilgi çekicidir. Ama, katıhalde, konjüge polimerler kararlılıklarını kaybedip bir araya toplanırlar. Bu sorunuaşmak için, konjüge polimerler molekül düzeyde izole olmuş tel haline getirilebilir.Bunu sağlamak için, konjüge polimerler, büyük içi boş kovan yapılarla sarmalanır.Bu çalışmada, konjüge polimerlerin sarmalanması iki metod izlenerek yapılmıştır. İlkmetodda, polimerin temel zincirleri büyük içi boş kovan yapılar içine sokulmuştur.Polipirol tabanlı südopolirotaksanlar bu yöntemle hazırlanmıştır. Pirol, CB(6) ilekompleks oluşturduktan sonra asidik ortamda FeCl3 ile kimyasal olarak yükseltgenerek1istenilen südopolirotaksan üretilmiştir. FT-IR, UV-VIS, Floresans ve H-NMRspektroskopi yöntemleri polipirol tabanlı südopolirotaksan oluşumunu kanıtlar.İkinci metodda ise, polimerlere bağlanmış yan zincirlerin rotaksanlanması vardır. Buamaçla, floren tabanlı monomerler seçilmiştir. Çünkü florenlerin 9. pozisyonunaistenilen fonksiyonel gruplar kolayca eklenebilir. Florenin 9 pozisyonuna uygun gruplareklendikten sonra, rotaksan oluşumu,CB(6)'nın katalizlediği 1,3-dipolar katılmareaksiyonu kullanılarak denenmiştir.Beyaz ışık diyotu inorganic-organik tabanlı iki malzemeden oluşan melez sistem ilehazırlanmıştır. Hazırlanan polimerler beyaz ışık üretiminde kullanılmıştır. Yüksek CRIindisli sonuçlar elde edilmiştir. Ayrıca, konjüge polimerlerin sıcaklığa maruzbırakıldıklarındaki kararlılılıkları FT-IR, UV-VIS ve Florasans spektroskopi yöntemleriile incelenmiştir.Anahtar Kelimeler: Südopolirotaksanlar, kukurbit[6]yuril(CB6), Suzuki BirleştirmeYöntemi, konjüge polimerler, polifloren, polipirol, beyaz ışık yayan diyot. ABSTRACTCONJUGATED POLYMERS BASED on POLYFLUORENE DERIVATIVES andPOLYPYRROLEÜNSAL KOLDEMİRM.S. in ChemistrySupervisor: Assist. Prof. Dr. Dönüş TuncelJuly 2007In this thesis, a series of polyfluorene based copolymers have been prepared via SuzukiCoupling for use in light emitting diodes (LEDs). Polyfluorene based polymers aresynthesized from different monomers. These polymers are characterized withspectroscopic techniques including FT-IR, UV-VIS, Fluorescence and 1H, 13C NMR.Conjugated polymers are attractive chemical structures inherently allowing chargetransport. However, in the solid state, conjugated polymers lack stability and formaggregates. To overcome this problem, conjugated polymers can be converted toinsulated molecular wires. This can be achieved by separation of the conjugatedpolymer chains by a macrocycle.In this study, encapsulation of conjugated polymers is tried with two methods. Firstmethod is to encapsulate the polymer main chain by macrocycles. Polypyrrole basedpolypseudorotaxane is prepared in this way. Pyrrole is complexed with thecucurbit[6]uril (CB(6)) and following chemical oxidation by FeCl3 in acidic mediumyields the desired polypseudorotaxane. Spectroscopic investigations such as FT-IR, UV-VIS, Fluorescence and 1H-NMR confirm the formation of polypyrrole basedpolypseudorotaxane.The second method involves the rotaxanation of the polymer side chains. For thispurpose, fluorene based monomers are chosen because the 9th position of fluorene canbe easily functionalized. After attaching suitable groups to the 9th position of fluorene,the rotaxane formation was attempted via 1,3 dipolar cycloaddition in the presence ofCB(6).A white light emitting diode is prepared using a hybrid inorganic and organic materialbased system. Prepared conjugated polymers were used in white light generation. Goodresults are obtained with high CRI indices. Also the thermal stability of the conjugatedpolymers is studied by FT-IR, UV-VIS and Fluorescence spectroscopic techniquesunder heat exposure.Keywords: Pseudopolyrotaxanes, cucurbit[6]uril, Suzuki Coupling, conjugatedpolymers, polyfluorene, polypyrrole, white light emitting diode. 109

ÖZETpH-DUYARLI ROTAKSANLAR VE POL PSÖDOROTAKSANLARHASAN BURAK T FT KKimya Bölümü Yüksek Lisans TeziTez Yöneticisi: Doç. Dr. Donus TuncelMay 2007Bu çalışmada, bir seri psödorotaksan, rotaksan ve polipsödorotaksan gibi mekaniksel olarakbirbiri içine geçmiş moleküller, uzun 12 metilen ve kısa 3 metilen alifatik aralık içeren çiftazido ve çift alkin monomerlerinin kendi aralarında CB6'in katalizlediği 1,3-dipolar siklokatılması yoluyla sentezlenmiştir.Bu yeni tip mekaniksel olarak birbiri içine geçmiş moleküllere ulaşmak amacıyla, ilk önceuygun monomer uniteleri tasarlanmış ve sentezlenmiştir. Bu monomerler çift azide ve çiftalkin grupları ile fonksiyonellenmiş, 3 ve 12 metilen aralık bulunduran çiftamin tuzlarıdır. Bumonomerlerin yapıları 1H, 13C-NMR, kütle ve FT-IR gibi spektroskopik tekniklerle veelemental analiz ile karakterize edilmiştir.Monomerlerin hazırlanmasında sonra, polipsödorotaksanlar CB6'in katalizlediği 1,3-dipolarsiklo eklenme yolu ile sentezlenmiştir. CB6 varlığında monomerler arasında adım adımbüyüme polimerizasyon tekniği uygulanmıştır. Ürünün proton NMR spektrumunda, 6.5 ppmde kapsüle olmuş triazol proton sinyalinin görülmesi, uygulanan reaksiyonun başarıylagerçekleştirildiği ve polipsödorotaksanın oluştuğunu göstermiştir. Ayrıca integrasyondeğelerinden herbir monomere karşılık molekülde bir CB6 olduğu gözlemlenmiştir.Üretilen polipsödorotaksan aynı zamanda matriks destekli lazer dezorpsiyon-iyonizasyon-uçuş zamanlı kütle spektrometresi kullanılarak incelenmiş ve en yüksek kütle 15600 Daolarak gözlemlenmiştir. Bu kütle temelde 12 CB6 bağlı yaklaşık 6 tekrar eden uniteden oluşanpolimer yığınına tekabül etmektedir.Polipsödorotaksanların sentezlenmesinden sonra, rotaksanların ve psödorotaksanların yenihazırlanmış çift alkin ve çift azido monomerleriyle yine CB6'in katalizlediği 1,3-Dipolar sikloeklenme reaksiyonu ile sentezlemesine geçilmiştir. Rotaksan sentezi için tert-butil içerendurducu unite kullanılmıştır. Sonuç olarak [3]rotaksan ve [3]psödorotaksan sentezlenmiş ve1H-NMR, FT-IR ve matriks destekli lazer dezorpsiyon-iyonizasyon-uçuş zamanlı kütle gibispektroskopik tekniklerle ve elemental analiz ile karakterize edilmiştir.Özellikle, CB6- tabanlı iki durumda kararlı [3]rotaksan, CB6'in katalizlediği 1,3-dipolar siklokatılma reaksiyonuyla yüksek verimli olarak üretilmiştir. Ek olarak bu yeni nesil moleküldeiki tanıma konumu bulunmakta ve tersinir moleküler kilit mekanizması gibidavranabilmektedir. Ayrıca baz, asid ve ısı koşullarında değişikliğe göre kendi içindekonformasyonal değişimler göstermektedir.Rotaksanlar, polipsödorotaksanlar, psödorotaksanlar,Anahtar Kelimeler:kukurbit[6]yuril(CB6), 1,3-Dipolar siklo katılma, n-alkandiamonyum tuzları, çiftazido,çiftalkin. ABSTRACTpH-RESPONSIVE ROTAXANES AND POLYPSEUDOROTAXANESHASAN BURAK T FT KM.S. in ChemistrySupervisor: Assist. Prof. Dr. Donus TuncelMay 2007In this study, a series of mechanically interlocked molecules like polypseudorotaxanes,rotaxanes and pseudorotaxanes have been synthesized via CB6 catalyzed 1,3-dipolarcycloaddition using diazide and dialkyne monomers, which contain long dodecyl and shortpropyl aliphatic spacers.To reach these novel interlocked molecules, first appropriate monomeric units were designedand synthesized. These monomeric units were diazido and dialkyne functionalized, propyl anddodecyl spacers containing, diamine salts. These monomers were fully characterized byspectroscopic techniques like 1H, 13C-NMR and FT-IR and elemental analysis.After the preparation of the monomers, polypseudorotaxanes were synthesized via CB6catalyzed 1,3-dipolar cycloaddition. The polymer formation proceeded through step-growthpolymerization in the presence of CB6. The reaction was followed by 1H-NMR spectroscopyeasily, because the appearance of a diagnostic peak at 6.5 ppm indicated the formation oftriazole ring, which joins the monomers.The polypseudorotaxane was also characterized by spectroscopic techniques like 1H, 13C-NMR and FT-IR and matrix assisted laser desorption time-of-flight mass spectrometry(MALDI-TOF MS). It produced a maximum mass at around 15600 Da which corresponds toabout six repeating units that is basically 12 CB6s threaded triazoles. The experimental resultsreveal that this polypseudorotaxane behaves as a pH-driven polymeric switch. Thus, whenamine groups are protonated at an appropriate pH, CB6s are located on the triazole rings dueto ion-dipole interaction, whereas at high pH they move onto the hydrophobic aliphaticspacer rather than slipping off the polypseudorotaxane.After the synthesis of the polypseudorotaxanes, a series of rotaxanes and pseudorotaxaneshave also been synthesized using the already prepared dialkyne and diazide monomers.Rotaxanation was also carried out via a 1, 3-dipolar cycloaddition reaction catalyzed by CB6.Among them, a bistable CB6-based [3]rotaxane synthesized through CB6 catalyzed 1,3-dipolar cycloaddition contains two recognition sites and behaves as a reversible molecularswitch. It exhibits conformational changes caused by the movement of rings under base, acidand heat stimuli from one location to the other.Keywords: Polyrotaxanes, rotaxanes, polypseudorotaxanes, pseudorotaxanes, cucurbit[6]uril,1,3-Dipolar cycloaddition, n-alkanediammonium salts, diazido, dialkyne. 94

Cataloged from PDF version of article. Cındır, Nesibe M.S.