Dithienopyrrole compound with twisted triphenylamine termini: Reversible near-infrared electrochromic and mechanochromic dual-responsive characteristics

作者：Zhang, Jing; Chen, Zhao; Yang, Lan; Hu, Fang; Yu, Guang-Ao; Yin, Jun^*; Liu, Sheng-Hua^*

来源：Dyes and Pigments, 2017, 136: 168-174.

DOI：10.1016/j.dyepig.2016.08.051

• Dithieno[3,2-b:2 ',3 '-d]pyrrole
• Triphenylamine
• Mechanochromic properties
• Electrochromic properties
• Fluorescence
• Density functional theory

A dithieno[3,2-b:2',3'-d]pyrrole-based luminogen 1 has been synthesized by appending two twisted triphenylamine units to the rigid conjugated dithieno[3,2-b:2',3'-d]pyrrole core. This compound exhibits reversible mechanochromic luminescence in the solid state and near-infrared electrochromic switching behavior in solution. A reversible switching in fluorescence color between yellow-green and green can be observed through mechanical grinding and vapor fuming of solid powdered 1, which involves an interconversion between a crystalline form and an amorphous phase according to X-ray diffraction analysis. The associated oxidized species of 1 show intense redox-switchable near-infrared absorption and different fluorescence colors in solution in spectroelectrochemical and luminescence measurements. Density functional theory calculations have confirmed that there is considerable electron delocalization between the dithieno[3,2-b:2',3'-d]pyrrole linker and two triphenylamine redox-active termini during the oxidation process.

• 出版日期2017-1
• 单位华中师范大学; 宁波大学