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Carbazole‐Fused Zinc(II)−Phthalocyanine Sensitizers
Author(s) -
Kimura Mutsumi,
Suzuki Hiroyuki,
Tohata Yuki,
Ikeuchi Takuro,
Yamamoto Satoshi,
Kobayashi Nagao
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600609
Subject(s) - carbazole , chemistry , phthalocyanine , photochemistry , homo/lumo , zinc , annulation , visible spectrum , acceptor , indoline , stereochemistry , organic chemistry , optoelectronics , molecule , materials science , physics , condensed matter physics , catalysis
Ring‐expanded zinc phthalocyanines 3 , 4 , and PcS27 were synthesized from new carbazole‐fused phthalonitriles 1 and 2 , and the effect of direct annulation of heterocycles with the phthalocyanine macrocycles on their optical and electrochemical properties were investigated. Carbazole‐fused zinc phthalocyanine 3 exhibited an intense Q band in the near‐infrared‐light region, owing to destabilization of the HOMO energy level, whilst low‐symmetry push–pull compound 4 showed a well‐defined split Q band, owing to splitting of the LUMO and LUMO+1 energy levels. Sensitizer PcS27 , which had a donor–π‐linker–acceptor structure, showed a panchromatic response from the visible‐light region to the near‐infrared‐light region if used as a light‐harvesting dye on TiO 2 electrodes for dye‐sensitized solar cells.