Transition-Metal-Free Oxidative C(sp2 )-H Hydroxylation of Terpyridines: A HOMO-Raising Strategy for the Construction of a New Super-Stable Terpyridine Chromophores

Jiang-Bo Huang; Xing-Feng Bai; Li Li; Zhan-Jiang Zheng; Zheng Xu; Yu-Ming Cui; Jian Cao; Li-Wen Xu

doi:10.1002/chem.201605793

Transition-Metal-Free Oxidative C(sp² )-H Hydroxylation of Terpyridines: A HOMO-Raising Strategy for the Construction of a New Super-Stable Terpyridine Chromophores

Chemistry. 2017 Mar 23;23(17):4055-4059. doi: 10.1002/chem.201605793. Epub 2017 Mar 9.

Authors

Jiang-Bo Huang¹, Xing-Feng Bai¹, Li Li¹, Zhan-Jiang Zheng¹, Zheng Xu¹, Yu-Ming Cui¹, Jian Cao¹, Li-Wen Xu^{1

2}

Affiliations

¹ Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, P. R. China.
² State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, P. R. China.

PMID: 28181312
DOI: 10.1002/chem.201605793

Abstract

Direct functionalization of terpyridines is an increasingly important topic in the field of dyes and catalysis as well as supramolecular chemistry, but its synthesis and transformation is usually challenging. Herein, a HOMO-raising strategy is reported for the construction of a super-stable novel terpyridine chromophores, in which the selective oxidation of terpyridines at its 3-position was determined successfully to the synthesis of phenol-functionalization of terpyridines (TPyOHs) bearing a hydrogen bonding group. The corresponding TPyOHs displayed strong aggregation-induced emission and exhibited highly selective and visual detection of Zn^II cation with a record green terpyridine-based luminophore with nanomolar sensitivity (125 nm).

Keywords: aggregation-induced emission; lithium; molecular recognition; selective oxidation; terpyridine.