Development of Imidazo[1,2- a]pyridine Derivatives with an Intramolecular Hydrogen-Bonded Seven-Membered Ring Exhibiting Bright ESIPT Luminescence in the Solid State

Toshiki Mutai; Tatsuya Muramatsu; Isao Yoshikawa; Hirohiko Houjou; Masaru Ogura

doi:10.1021/acs.orglett.9b00455

Development of Imidazo[1,2- a]pyridine Derivatives with an Intramolecular Hydrogen-Bonded Seven-Membered Ring Exhibiting Bright ESIPT Luminescence in the Solid State

Org Lett. 2019 Apr 5;21(7):2143-2146. doi: 10.1021/acs.orglett.9b00455. Epub 2019 Mar 28.

Authors

Toshiki Mutai¹, Tatsuya Muramatsu¹, Isao Yoshikawa¹, Hirohiko Houjou¹, Masaru Ogura¹

Affiliation

¹ Department of Materials and Environmental Science, Institute of Industrial Science , The University of Tokyo , 4-6-1, Komaba , Meguro-ku, Tokyo 153-8505 , Japan.

PMID: 30920228
DOI: 10.1021/acs.orglett.9b00455

Abstract

Imidazo[1,2- a]pyridine derivatives with different hydroxyaryl units (1-3), which could potentially form an intramolecular hydrogen-bonded seven-membered ring in either a planar or a twisted conformation, were newly developed, and the effect of conformation and steric repulsion on the excited-state intramolecular proton transfer (ESIPT) luminescence was evaluated. Among them, 1 and 2 formed an intramolecular hydrogen-bonded seven-membered ring in the crystalline state and exhibited efficient ESIPT luminescence in the solid state (quantum yield up to 0.45).

Publication types

Research Support, Non-U.S. Gov't