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Triarylisocyanurate‐Based Fluorescent Two‐Photon Absorbers
Author(s) -
Gautier Yohan,
Argouarch Gilles,
Malvolti Floriane,
Blondeau Benjamin,
Richy Nicolas,
Amar Anissa,
Boucekkine Abdou,
Nawara Krzysztof,
Chlebowicz Katarzyna,
Orzanowska Grażyna,
Dudek Marta,
Matczyszyn Katarzyna,
Samoc Marek,
BlanchardDesce Mireille,
Mongin Olivier,
Waluk Jacek,
Paul Frédéric
Publication year - 2020
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000036
Subject(s) - chromophore , substituent , fluorescence , intramolecular force , photochemistry , excited state , chemistry , singlet state , phenylene , absorption (acoustics) , two photon absorption , excitation , population , materials science , stereochemistry , polymer , atomic physics , organic chemistry , laser , physics , electrical engineering , demography , quantum mechanics , sociology , optics , composite material , engineering
The synthesis and characterization of six triarylisocyanurates, featuring 2,7‐fluorenyl or 9,10‐anthracenyl groups incorporated in their peripheral arms are reported. Photophysical studies reveal that these new octupolar derivatives are more fluorescent ( Φ F ≥0.60 for all new compounds except for 1,3,5‐tri(9H‐fluoren‐2‐yl)‐1,3,5‐triazinane‐2,4,6‐trione 3 ) and present a red‐shifted lowest absorption and emission compared to their known phenyl analogues of comparable size. Depending on the nature of the terminal substituent, fast intramolecular energy transfer among the three arms or localization of the excitation on a single branch occurs after population of their first singlet excited state. The latter effect was only observed in the presence of strongly electron‐releasing substituents in polar media. These new chromophores are also better two‐photon absorbers than the 1,4‐phenylene‐based isocyanurates reported so far, with cross sections σ 2 ≥500 GM at 770 nm for 4‐NPh 2 the fluorenyl group containing ( 13 ) and the anthracenyl group containing ( 14 ) chromophores. All these spectroscopic features, analyzed with the help of quantum chemical calculations, are crucial for the design of new biphotonic fluorescent dyes.