N‐Boc‐Indolylbenzothiadiazole Derivatives: Efficient Full‐Color Solid‐State Fluorescence and Self‐Recovering Mechanochromic Luminescence. Issue 13 (17th June 2016)

• Record Type: Journal Article
• Authors: Ito, Suguru; Yamada, Takeshi; Taguchi, Tomohiro; Yamaguchi, Yoshitaka; Asami, Masatoshi
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 13(2016)
• Page Start: 1963
• Page End: 1970
• Publication Date: 2016-06-17
• Subjects: donor–acceptor systems -- dyes/pigments -- fluorescence -- luminescence -- mechanofluorochromism -- solid-state structures; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201600526
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: Herein, the solid‐state emission with good fluorescence quantum yields of N ‐Boc‐indolylbenzothiadiazoles as a new class of fluorophores is described. Their solid‐state emission covers the wide range of the visible spectrum and the emission color can be tuned easily by changing the substituents on the two heteroaromatic rings. Among these, 3‐methylindolyl derivatives exhibit moreover autonomously self‐recovering mechanochromic luminescence, whereby the original solid‐state emission could be recovered spontaneously at room temperature after exposure to a mechanical stimulus. The emission color, as well as the recovery time for the color change could be tuned via the introduction of different substituents on the benzothiadiazole ring. We propose that the mechanism of the autonomously self‐recovering mechanochromic luminescence of 3‐methylindolylbenzothiadiazoles is based on a partial amorphization of the crystals upon exposure to the mechanical stimulus, followed by autonomous recovering in the form of recrystallization. Abstract : On the road to recovery : The full‐color solid‐state emission of N ‐Boc‐indolylbenzothiadiazoles as a new class of solid‐state emissive fluorophores is described. Among these, 3‐methylindolyl derivatives exhibit moreover autonomously self‐recovering mechanochromic luminescence, whereby the original solid‐state emission could be recovered spontaneously at room temperature after exposure to a mechanical stimulus.