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Benzothiadiazole‐Substituted Aza‐BODIPY Dyes: Two‐Photon Absorption Enhancement for Improved Optical Limiting Performances in the Short‐Wave IR Range
Author(s) -
David Sylvain,
Chang HaoJung,
Lopes Cesar,
Brännlund Carl,
Le Guennic Boris,
Berginc Gérard,
Van Stryland Eric,
Bondar Mykailo V.,
Hagan David,
Jacquemin Denis,
Andraud Chantal,
Maury Olivier
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004899
Subject(s) - bodipy , intramolecular force , absorption (acoustics) , photochemistry , two photon absorption , materials science , moiety , delocalized electron , absorption spectroscopy , fluorescence , chemistry , optics , organic chemistry , laser , physics , composite material
Aza‐boron dipyrromethenes (aza‐BODIPYs) presenting a benzothiadiazole substitution on upper positions are described. The strong electron‐withdrawing effect of the benzothiadiazole moiety permits enhancement of the accepting strength and improves the delocalization of the aza‐BODIPY core to attain a significant degree of electronic communication between the lower donating groups and the upper accepting groups. The nature of the intramolecular charge transfer is studied both experimentally and theoretically. Linear spectroscopy highlighted the strongly redshifted absorption and emission of the synthesized molecules with recorded fluorescence spectra over 1000 nm. Nonlinear optical properties were also investigated. Strong enhancement of the two‐photon absorption of the substituted dyes compared with the unsubstituted one (up to 4520 GM at 1300 nm) results in an approximately 15–20 % improvement of the optical power limiting performances. These dyes are therefore a good starting point for further improvement of optical power limiting in the short‐wave IR range.