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Aggregation‐Induced Emission‐Active Carbazolyl‐Modified Benzo[4,5]thiazolo[3,2‐ c ]oxadiazaborinines as Mechanochromic Fluorescent Materials
Author(s) -
Potopnyk Mykhaylo A.,
Volyniuk Dmytro,
Luboradzki Roman,
Lazauskas Algirdas,
Grazulevicius Juozas Vidas
Publication year - 2021
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.202100239
Subject(s) - carbazole , chemistry , benzothiazole , tetrahydrofuran , acceptor , photochemistry , fluorescence , intramolecular force , aggregation induced emission , polymer chemistry , organic chemistry , physics , quantum mechanics , solvent , condensed matter physics
Two highly emissive donor‐acceptor type organoboron dyes, based on carbazole donor and benzothiazole‐fused oxadiazaborinine acceptor, were designed and synthesized. The compounds demonstrated high positive solvatofluorochromism in solutions, caused by intramolecular charge transfer. Such carbazolyl‐containing N,O‐chelated organoboron dyes exhibited aggregation‐induced emission properties: in tetrahydrofuran/water mixture with a high water amount, they formed highly emissive nanoaggregates. Both materials demonstrated efficient solid‐state emission in the crystalline and thin film state (PLQY of up to 48 %), as well as significant mechanofluorochromic properties (Δλ em =30–38 nm). Moreover, a compound with unsubstituted carbazole unit was isolated as two distinct crystalline polymorphs with different photophysical properties.