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Improved Spectral Coverage and Fluorescence Quenching in Donor–acceptor Systems Involving Indolo[3‐2‐b]carbazole and Boron‐dipyrromethene or Diketopyrrolopyrrole
Author(s) -
Khetubol Adis,
Van Snick Sven,
Clark Melissa L.,
Fron Eduard,
CoutiñoGonzález Eduardo,
Cloet Arvid,
Kennes Koen,
Firdaus Yuliar,
Vlasselaer Maarten,
Leen Volker,
Dehaen Wim,
Van der Auweraer Mark
Publication year - 2015
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/php.12437
Subject(s) - photochemistry , fluorescence , bodipy , carbazole , acceptor , quenching (fluorescence) , quantum yield , chemistry , absorption (acoustics) , materials science , absorption spectroscopy , physics , quantum mechanics , composite material , condensed matter physics
A novel π ‐conjugated triad and a polymer incorporating indolo[3,2‐ b ]‐carbazole ( ICZ ) and 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene ( BODIPY ) were synthesized via a Sonogashira coupling. Compared to the parent BODIPY the absorption and fluorescence spectrum were for both compounds broader and redshifted. The redshift of the fluorescence and the decrease of the fluorescence quantum yield and decay time upon increasing solvent polarity were attributed to the formation of a partial charge‐transfer state. Upon excitation in the ICZ absorption band the ICZ fluorescence was quenched in both compounds mainly due to energy transfer to the BODIPY moiety. In a similar ICZ – π – DPP polymer (where DPP is diketopyrrolopyrrole), a smaller redshift of the absorption and fluorescence spectra compared to the parent DPP was observed. A less efficient quenching of the ICZ fluorescence in the ICZ – π – DPP polymer could be related to the unfavorable orientation of the transition dipoles of ICZ and DPP . The rate constant for energy transfer was for all compounds an order of magnitude smaller than predicted by Förster theory. While in a solid film of the triad a further redshift of the absorption maximum of nearly 100 nm was observed, no such shift was observed for the ICZ – π – BODIPY polymer.