Aggregation-induced emission (AIE)-active phenanthrenequinone hydrazone-based dyes with reversible mechanofluochromism. (September 2019)

• Record Type: Journal Article
• Authors: Yan, Xiaojing; Zhu, Pengcheng; Li, Yang; Yuan, Shuang; Lan, Haichuang; Xiao, Shuzhang
• Is Part Of: Materials today communications. Volume 20(2019)
• Publication Date: 2019-09
• Subjects: Luminescence -- Optical materials and properties -- Phenanthrenequinone hydrazone -- AIE -- Mechanochromism; Materials science -- Periodicals; 620.11
• DOI: 10.1016/j.mtcomm.2019.100565
• Languages: English
• ISSNs: 2352-4928

Abstract

Graphical abstract: Highlights: Two phenanthrenequinone hydrazone-based compounds with AIE characters were efficiently synthesized. These compounds were mechanochromic, and their emissions can be reversibly tuned by grinding and solvent fuming. The mechanochromic fluorescences were owing to the stimuli-induced changes of intermolecular π-π interactions. Abstract: Two phenanthrenequinone hydrazone-based compounds (PHPO and NHPO ) were efficiently synthesized via a "one-pot" nucleophilic addition reaction, and they exhibited aggregate-induced fluorescence enhancement characteristics. X-ray single crystal analysis of NHPO indicates that the molecule is highly planar, and intense intermolecular π-π interactions exist to facilitate the formation of dimeric structure, which could significantly quench the fluorescence. Both compounds are responsive to mechanical force, and their emissions can be reversibly turned "off" and "on" by grinding and solvent fuming (or heating). The PXRD profiles demonstrated a transformation between crystalline and amorphous state upon grinding and fuming.