Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole-Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

authored by

Dominik Göbel, Pascal Rusch, Daniel Duvinage, Tim Stauch, Nadja-C Bigall, Boris J. Nachtsheim

Abstract

Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.

Organisation(s)

Section Functional nanostructures from assembled colloidal nanoparticles
PhoenixD: Photonics, Optics, and Engineering - Innovation Across Disciplines
Institute of Physical Chemistry and Electrochemistry

External Organisation(s)

University of Bremen

Type

Article

Journal

The journal of organic chemistry

Volume

86

Pages

14333-14355

No. of pages

23

ISSN

0022-3263

Publication date

05.11.2021

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Organic Chemistry

Electronic version(s)

https://doi.org/10.1021/acs.joc.1c00846 (Access: Closed)