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A comprehensive study of the effect of intraphase microstructure on organic photovoltaic (OPV) device performance is undertaken. Utilizing a bilayer device architecture, a small molecule donor (TIPS-DBC) is deposited by both spin-coating and by thermal evaporation in vacuum. The devices are then completed by thermal evaporation of C, an exciton blocking layer and the cathode. This bilayer approach enables a direct comparison of device performance for donor layers in which the same material exhibits subtle differences in microstructure. The electrical performance is shown to differ considerably for the two devices. The bulk and interfacial properties of the donor layers are compared by examination with photoelectron spectroscopy in air (PESA), optical absorption spectroscopy, charge extraction of photo-generated charge carriers by linearly increasing voltage (photo-CELIV), time-resolved photoluminescence measurements, X-ray reflectometry (XR), and analysis of dark current behavior. The observed differences in device performance are shown to be influenced by changes to energy levels and charge transport properties resulting from differences in the microstructure of the donor layers. Importantly, this work demonstrates that in addition to the donor/acceptor microstructure, the intraphase microstructure can influence critical parameters and can therefore have a significant impact on OPV performance. The influence of intraphase microstructure on the performance of organic photovoltaics (OPVs) is studied utilizing a bilayer (planar heterojunction) device architecture. Devices in which the donor layer exhibits subtle differences in microstructure are compared, and these differences are shown to affect critical parameters (energy levels, charge transport properties) having a significant impact on performance. Copyright

A variety of the title imidazopyridazine derivatives are synthesized and evaluated for their in vitro anthelmintic activity.

Reductive alkylation of methyl 3,5-dimethoxybenzoate with the dibromoalkane and the bromochloroalkane derivatives (4a-d) and (4e-g) afforded, after acid hydrolysis, the corresponding methyl 1-( haloalkyl )-3-methoxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (6a-g). Reaction of (6a-c) with lithium diisopropylamide afforded methyl 3-methoxy-5-oxobicyclo[4.2.0]oct-3-ene- 1-carboxylate (2a), methyl 5-methoxy-7-oxo-1,2,3,4,7,7a-hexahydro-3aH-indene-3a-carboxylate (2b) and methyl 6-methoxy-8-oxo-1,3,4,5,8,8a-hexahydronaphtha1ene-4a(2 H)- carboxylate (2c), respectively. Compounds (2b) and (2c) were also obtained from the reaction of (6f) and (6g) with lithium diisopropylamide . Compounds (2a) and (2b) were each obtained as a single bridgehead isomer, the relative stereochemistry of ring fusion of which was assigned as cis on the basis of semiempirical molecular orbital calculations. Compound (2c) was obtained as a mixture of cis-and trans-fused bridgehead isomers. The ester (2b) was converted into the herbicide methyl 5,7-dioxo-6-[1-[(prop-2-enyloxy) imino ] butyl]octahydro-3aH-indene-3a-carboxylate (3a).

Reaction of pyridine-3-carbaldehyde methylhydrazone with 1,1'-carbonylbis-1H-imidazole afforded (E)-1'-methyl-2'-(3"-pyridyl) methylidene ]-1H-imidazole-1-carbohydrazide (2). Reaction of (2) with ethylamine, ethanol, ethanethiol, hydrazine monohydrate and methoxyamine afforded the corresponding semicarbazide, carbazate, thiocarbazate, carbonohydrazide and 4-methoxysemicarbazide derivatives (3a-d,g). Reaction of (2) with methylhydrazine gave the carbonohydrazide derivative (3f) together with 2,4-dimethyl-6-(3'-pyridyl)-1,4,5,6-tetrahydro-1,2,4,5-tetrazin-3(2H)-one (4a). The preparation of (E)-3-[(3'-pyridyl) methylideneamino ]oxazolidin-2-one (5a) and (E)-3-[(3'-pyridyl) methylideneamino ]tetrahydro-2H-1,3-oxazin-2-one (5b) is described.

Reaction of the methyl 2-(phenylmethylidene)hydrazinecarboximidothioate derivatives (3a–d) and (6a,b) with iron(III) chloride afforded the 5-methylsulfanyl-3-phenyl-4H-1,2,4-triazole derivatives (4a–d) and the 5-methylsulfanyl-3-phenyl-1H-1,2,4-triazole derivatives (7a,b). This reaction was extended to the synthesis of the 3-phenyl-5,6-dihydrothiazolo[2,3-c]-1,2,4-triazole derivatives (10a,b) and the 3-phenyl-6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3]thiazine derivatives (10c,d). Reaction of 5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (12a) with 1,2-dibromoethane gave (10a) together with the isomeric 2-(3-chlorophenyl)-5,6-dihydrothiazolo[3,2-b][1,2,4]triazole (13a); similarly, reaction of (12a) with 1,3-dibromopropane afforded (10c) along with 2-(3-chlorophenyl)-6,7-dihydro-5H-[1,2,4]triazolo[5,1-b][1,3]thiazine (13b). The use of nickel peroxide and lead tetraacetate in place of iron(III) chloride was investigated for some of these oxidative cyclization reactions.

Reductive alkylation of 3,5-dimethoxybenzoic acid with haloalkanes afforded the 1-alkyl- 3,5-dimethoxycyclohexa-2,5-diene-1-carboxylic acid derivatives (3a-e) which, upon esterification and hydrolysis, furnished methyl 1-alkyl-3-hydroxy-5-oxocyclohex-3-ene-l-carboxylate derivatives (4f-j). Reaction of (4f-j) with butyric anhydride gave methyl 1-alkyl-4-butyryl- 3-hydroxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (6a-e) which were converted into methyl 1-alkyl-4-[1-( ethoxyimino )butyl]-3-hydroxy-5-oxocyclohex-3-ene-1-carbo xyate derivatives (2a-e). Similarly, the oxime O-ether derivative (2f) was prepared from the amide (41), obtained from reaction of (3b) with N,N′- carbonyldiimidazole and dimethylamine followed by hydrolysis.

Synthese en 12 etapes avec un rendement de 6% a partir du pyrrolidino-1 cyclopentene. L'addition Diels Alder a haute pression permet d'obtenir la configuration absolue des jatropholones