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1,2‐Disubstituted 3,3,4,4,5,5‐Hexafluorocyclopentenes as Bent Light‐Emitting π‐Conjugated Luminophores
Author(s) -
Yamada Shigeyuki,
Nishizawa Akito,
Agou Tomohiro,
Kubota Toshio,
Konno Tsutomu
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901794
Subject(s) - chemistry , photoluminescence , conjugated system , photochemistry , alkoxy group , benzene , wavelength , absorption (acoustics) , absorption spectroscopy , optoelectronics , organic chemistry , materials science , optics , polymer , alkyl , composite material , physics
Herein, a series of 1,2‐disubstituted 3,3,4,4,5,5‐hexafluorocyclopentene derivatives is synthesized from the commercially available octafluorocyclopentene via addition‐elimination reactions, and their photophysical properties are investigated in detail. 1,2‐Bis[2‐(4‐alkoxyaryl)ethyn‐1‐yl]‐3,3,4,4,5,5‐hexafluorocyclopentene exhibits UV‐absorption at 345 nm in CH 2 Cl 2 and deep blue photoluminescence (PL). The PL properties of these derivatives, including color and maximum wavelength ( λ PL ), are strongly affected by the electron‐density distribution induced by the electronic characteristics of the alkoxy‐substituents at the 4‐position of the benzene ring, with more electron‐donating substituents resulting in a larger shift of λ PL to longer wavelengths. Note that the present light‐emitting π‐conjugated luminophores also exhibit relatively strong PL in the crystalline state, where λ PL shifts can be introduced by modulation of the terminal alkoxy‐chain length, resulting in different PL colors from light‐blue to orange.