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Carbazole-Terpyridine Donor-Acceptor Dyads with Rigid π-Conjugated Bridges
- Source :
- ChemPlusChem 84 (2019): 1–14. doi:10.1002/cplu.201900213, info:cnr-pdr/source/autori:Matteucci, Elia; Baschieri, Andrea; Sambri, Letizia; Monti, Filippo; Pavoni, Eleonora; Bandini, Elisa; Armaroli, Nicola/titolo:Carbazole-Terpyridine Donor-Acceptor Dyads with Rigid ?-Conjugated Bridges/doi:10.1002%2Fcplu.201900213/rivista:ChemPlusChem/anno:2019/pagina_da:1/pagina_a:14/intervallo_pagine:1–14/volume:84
- Publication Year :
- 2019
-
Abstract
- A series of molecules in which 9H-carbazole (electron donor, D) and 2,2':6',2''-terpyridine (electron acceptor, A) are connected through rigid π-conjugated bridges (D-π-A systems) have been synthesized and their photophysical properties examined in detail, with the support of DFT calculations. The bridges are made of different sequences of ethynylene, phenylene, and anthracene groups. The synthetic strategies involve condensation of 2-acetylpyridine with the aromatic aldehyde moiety on different functionalized π-conjugated bridges and couplings with carbazole derivatives. The system incorporating anthracene in the bridge shows the typical absorption and emission fingerprints of this polycyclic hydrocarbon. The other systems have HOMOs and LUMOs centred, respectively, over the carbazole and the bridge and exhibit solvatochromic charge-transfer (CT) luminescence with high photoluminescence yield up to 70 %, except when an ethynylene unit is directly attached to the carbazole ring, due to a trans-bent non-emissive π-σ* excited state.
- Subjects :
- Materials science
donor-acceptor dyads
Electron donor
010402 general chemistry
01 natural sciences
chemistry.chemical_compound
Phenylene
carbazole
Moiety
π-conjugated systems
chemistry.chemical_classification
Anthracene
010405 organic chemistry
Carbazole
fluorescence
terpyridines
Solvatochromism
General Chemistry
?-conjugated systems
Electron acceptor
Carbazole, terpyridine, π‐conjugated bridges, D‐π‐A systems
0104 chemical sciences
Crystallography
chemistry
Terpyridine
Subjects
Details
- ISSN :
- 21926506
- Volume :
- 84
- Issue :
- 9
- Database :
- OpenAIRE
- Journal :
- ChemPlusChem
- Accession number :
- edsair.doi.dedup.....7d59e0b87449a1e5178361ff8d42eef5