Indolylbenzothiadiazoles with varying substituents on the indole ring: a systematic study on the self-recovering mechanochromic luminescence

Abstract

A series of mechanochromic fluorophores exhibited self-recovering mechanochromic luminescence properties with varying emission color and recovery times.

Indolylbenzothiadiazoles as highly tunable fluorophores for imaging lipid droplet accumulation in astrocytes and glioblastoma cells

“…1, top). 25,26 Thus, in this work we wanted to explore their utility as imaging agents for uorescent cell microscopy and also study how different N-substituents on the indole motif affect the photophysical properties (Fig. 1, bottom).…”

Recent Advances in Mechanochromic Luminescence of Organic Crystalline Compounds

“…Notably, 3-alkyl-substituted derivatives exhibited self-recovering MCL, and recovery time of this MCL could be controlled by the substituents. 19,20 For example, the ground samples of N-methyl-substituted 10d quickly recovered to the original state within 10 s, whereas N-benzoyl-substituted 10b required 2 h. Differential scanning calorimetry (DSC) analysis suggested that the relatively high glass-transition temperature above room temperature might be the origin of longer recovery times. Compared with the non-MCL dye 10e, 3-methylsubstituted 10a exhibited slipped antiparallel stacks of benzothiadiazole rings.…”

“…Based on the molecular design principle of indolylbenzothiadiazoles 10, 19,20 the author and coworkers developed novel donor-acceptor-type MCL compounds 17 by using phenanthroimidazole ring as the electron-donating heteroaromatic group in 2019 (Figure 4d). 32 Compounds 17af were highly emissive both in toluene and in the crystalline state, and exhibited bathochromically shifted MCL except for methoxy-substituted derivative 17c.…”

Mechanoresponsive Material of AIE-Active 1,4-Dihydropyrrolo[3,2-b]pyrrole Luminophores Bearing Tetraphenylethylene Group with Rewritable Data Storage

“…Mechanofluorochromic materials as a kind of “smart material’’ have its potential applications in mechanosensors, fluorescence switches, and data storage so on [17,18,19,20,21,22,23,24,25,26]. Recently, rationally controlling the design of molecular mechanofluorochromic behavior is still a huge challenging, two main problems restrict the development of this kind of materials: the lack of deep understanding for the structure-property relationship of such materials and the fluorescent quenching effect in the solid state [27,28,29,30,31]. It is exciting that a major breakthrough came from an unusual aggregation-induced emission (AIE) phenomenon in the study of 1-methyl-1,2,3,4,5-pentaphenylsilole [32].…”