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Carbazole‐Terpyridine Donor‐Acceptor Dyads with Rigid π‐Conjugated Bridges
Author(s) -
Matteucci Elia,
Baschieri Andrea,
Sambri Letizia,
Monti Filippo,
Pavoni Eleonora,
Bandini Elisa,
Armaroli Nicola
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201900213
Subject(s) - carbazole , anthracene , conjugated system , moiety , photochemistry , chemistry , solvatochromism , acceptor , excited state , terpyridine , molecule , stereochemistry , organic chemistry , polymer , physics , nuclear physics , metal , condensed matter physics
A series of molecules in which 9 H ‐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.