Synthesis, photophysical properties and two-photon absorption of benzothiazole/benzoxazole π-expanded carbazole dyes. (August 2022)

• Record Type: Journal Article
• Authors: Sun, Lei; Wang, Xiaoyu; Fleurat-Lessard, Paul; Gros, Claude P.; Bolze, Frédéric; Xu, Haijun
• Is Part Of: Dyes and pigments. Volume 204(2022)
• Publication Date: 2022-08
• Subjects: Benzothiazole -- Benzoxazole -- Carbazole -- Photophysical properties -- Two-photon absorption; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2022.110447
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: We report the synthesis and spectroscopic characterization (NMR, HRMS) of a series of benzazole derivatives with different carbazole substituents. The photophysical properties of these molecules were investigated in several solvents of different polarity by UV–vis absorption and fluorescence spectroscopy. These dyes show strong absorption bands in the near ultraviolet region, fluorescence emission with high quantum yields in the blue-green as well as large Stokes' shifts. Two-photon absorption properties were recorded and all of the dyes show moderate TPA cross sections in the 700–800 nm zone. Molecular modeling was also used to explain spectroscopic behavior of these dyes. Interestingly, they possess high thermal stability. Graphical abstract: Benzothiazole/benzoxazole π-expanded carbazole dyes were prepared and showed high thermal stability. Image 1 Highlights: Benzothiazole/benzoxazole π-expanded carbazole dyes were prepared by one step reaction. Photophysical characterizations and two-photon absorption were performed. Calculations show the variation of conjugation for the different systems . The dyes display high thermal stability.