Janus-Type ESIPT Chromophores with Distinctive Intramolecular Hydrogen-bonding Selectivity

Yahui Chen, Sheng Lu, Syed Ali Abbas Abedi, Minseok Jeong, Haidong Li, Myung Hwa Kim, Sungnam Park, Xiaogang Liu, Juyoung Yoon, Xiaoqiang Chen

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Excited-state intramolecular proton transfer (ESIPT)-based solid luminescent materials with multiple hydrogen bond acceptors (HBAs) remain unexplored. Herein, we introduced a family of Janus-type ESIPT chromophores featuring distinctive hydrogen bond (H-bond) selectivity between competitive HBAs in a single molecule. Our investigations showed that the central hydroxyl group preferentially forms intramolecular H-bonds with imines in imine-modified 2-hydroxyphenyl benzothiazole (HBT) chromophores but tethers the benzothiazole moiety in hydrazone-modified HBT chromophores. Imine-derived HBTs generally exhibit higher fluorescence efficiency, while hydrazone-derived HBTs show a reduced overlap between the absorption and fluorescence bands. Quantum chemical calculations unveiled the molecular origins of the biased intramolecular H-bonds and their impact on the ESIPT process. This Janus-type ESIPT chromophore skeleton provides new opportunities for the design of solid luminescent materials.

Original languageEnglish
Article numbere202311543
JournalAngewandte Chemie - International Edition
Volume62
Issue number40
DOIs
StatePublished - 2 Oct 2023

Bibliographical note

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

Keywords

  • Competitive Hydrogen Bond Acceptors
  • Excited-State Intramolecular Proton Transfer
  • Janus-Type
  • Quantum Chemical Calculations

Fingerprint

Dive into the research topics of 'Janus-Type ESIPT Chromophores with Distinctive Intramolecular Hydrogen-bonding Selectivity'. Together they form a unique fingerprint.

Cite this