Carbazole-modified thiazolo[3, 2-c][1, 3, 5, 2]oxadiazaborinines exhibiting aggregation-induced emission and mechanofluorochromism. Issue 2 (14th December 2020)

• Record Type: Journal Article
• Authors: Potopnyk, Mykhaylo A.; Kravets, Mykola; Luboradzki, Roman; Volyniuk, Dmytro; Sashuk, Volodymyr; Grazulevicius, Juozas Vidas
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 2(2020)
• Page Start: 406
• Page End: 415
• Publication Date: 2020-12-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob02225j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Two novel AIE-active donor–acceptor organoboron complexes with a carbazole donor unit are developed and their morphology-dependent solid-state fluorescence properties are established. Abstract : Two highly emissive carbazole-containing thiazole-fused oxadiazaborinines were designed and synthesized. These N, O -chelated organoboron dyes displayed large Stokes shifts and remarkable solvatofluorochromism in solutions, as well as good thermal stability and comparatively high photoluminescence quantum yields (up to 34%) in the solid state. The presence of a carbazole donor unit, linked with the oxadiazaborinine acceptor via a phenyl linker, restricted intramolecular rotation, leading to enhanced aggregation-induced emission properties of the compounds: in THF/water mixtures with a large water percentage, they demonstrated the formation of emissive nanoaggregates with an average size of 79 and 89 nm for complexes 2 and 3, respectively. The introduction of bulky tert -butyl groups attached to the carbazole moiety induced significant mechanofluorochromic properties of the compounds.