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Benzo[1,2‐ d :4,5‐ d ′]bisimidazoles as a Convenient Platform Towards Dyes that are Capable of Excited‐State Intramolecular Proton Transfer and of Two‐Photon Absorption
Author(s) -
Tasior Mariusz,
Hugues Vincent,
BlanchardDesce Mireille,
Gryko Daniel T.
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200539
Subject(s) - intramolecular force , fluorescence , excited state , chemistry , absorption (acoustics) , bioconjugation , photochemistry , stokes shift , proton , two photon absorption , derivative (finance) , stereochemistry , materials science , combinatorial chemistry , atomic physics , physics , optics , quantum mechanics , composite material , laser , financial economics , economics
Abstract New, strongly fluorescent benzo[1,2‐ d :4,5‐ d′ ]bisimidazoles have been prepared by the reaction of Bandrowski′s base with various aldehydes. Their structures were carefully designed to achieve efficient excited‐state intramolecular proton transfer and good two‐photon‐absorption (2PA) cross‐sections. Functional dyes that possessed both high fluorescence quantum yields and large Stokes shifts were prepared. A π‐expanded D‐A‐D derivative that possessed Φ fl =50 % and σ 2 =230 GM in the spectroscopic area of interest for biological imaging is an excellent candidate as a fluorescent probe. Thanks to the presence of two reactive amino groups, such compounds can be easily transformed into probes for bioconjugation. All of these benzo[1,2‐ d :4,5‐ d ′]bisimidazoles were also strongly fluorescent in the solid state.