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Mechanochromic Luminescence of 2,6-Bis(4-biphenyl)isonicotinic Acid via Interconversion of Classical/Frustrated Brönsted Pair

Hongyan Zhao, Linwei Huang, Yedong Wang, Kai Feng, Yunhao Chang, Shiqing Huang, Chenxing Ma, Xiaoyu Yan

2021The Journal of Organic Chemistry10 citationsDOI

Abstract

A practicable strategy to a reversible mechanochromic material featuring interconversion of classical/frustrated Brönsted pairs has been established. We report the mechanochromic property of 2,6-bis(4-biphenyl)isonicotinic acid (1), which features a frustrated Brönsted pair in the crystalline form and a classical Brönsted pair after grinding. A large mechanochromic shift was found from 428 to 505 nm. In addition, compound 1 also exhibits acidochromic behavior, which further proves that the formation of an acid-base interaction is responsible for the mechanochromic phenomenon.

Topics & Concepts

Isonicotinic acidChemistryBiphenylBrønsted–Lowry acid–base theoryLuminescencePhotochemistryCatalysisOrganic chemistryMaterials scienceOptoelectronicsHydrazideLuminescence and Fluorescent MaterialsPorphyrin and Phthalocyanine ChemistryCrystallography and molecular interactions
Mechanochromic Luminescence of 2,6-Bis(4-biphenyl)isonicotinic Acid via Interconversion of Classical/Frustrated Brönsted Pair | Litcius