Mechanically induced single-molecule white-light emission of excited-state intramolecular proton transfer (ESIPT) materials
- 18 February 2021
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Mater. Horiz.
- Vol. 8 (5), 1499-1508
- https://doi.org/10.1039/d0mh02032j
Abstract
Described herein is the first example of mechanically induced single-molecule white-light emission based on excited-state intramolecular proton transfer (ESIPT) materials. Mechanism of mechanochromism is clearly disclosed by powder and single crystal X-ray diffraction (XRD) data, infrared spectroscopy, and fluorescence up-conversion measurement, etc. 2-(2'-Hydroxyphenyl)oxazole (6b) with a herringbone packing motif exhibits a predominant keto-form emission, giving off yellowish-green fluorescence. Mechanical grinding transforms the herringbone packing motif into a brickwork packing motif, decreases intermolecular distances, which results in an enhanced intermolecular charge-transfer interaction, and therefore changes ESIPT dynamics, leading to an enhanced enol-form emission and white fluorescence. Herringbone-packing 6b is thermodynamically more stable than brickwork-packing 6b. Thus, the latter can convert to the former by solvent fuming or thermal annealing.Keywords
Funding Information
- National Natural Science Foundation of China (No. 22071162 and 21672154)
This publication has 54 references indexed in Scilit:
- Molecular Packing: Another Key Point for the Performance of Organic and Polymeric Optoelectronic MaterialsAccounts of Chemical Research, 2020
- Polymorph‐Dependent Thermally Activated Delayed Fluorescence Emitters: Understanding TADF from a Perspective of Aggregation StateAngewandte Chemie, 2019
- Boron-based stimuli responsive materialsChemical Society Reviews, 2019
- Transient‐Ligand‐Enabled ortho‐Arylation of Five‐Membered Heterocycles: Facile Access to Mechanochromic MaterialsAngewandte Chemie, 2018
- Molecular Engineering of Mechanochromic Materials by Programmed C–H Arylation: Making a Counterpoint in the Chromism TrendJournal of the American Chemical Society, 2016
- Mechanoresponsive Luminescent Molecular Assemblies: An Emerging Class of MaterialsAdvanced Materials, 2015
- Luminescent Chromism of Boron Diketonate Crystals: Distinct Responses to Different StressesAdvanced Materials, 2015
- Smart responsive phosphorescent materials for data recording and security protectionNature Communications, 2014
- Dye-containing polymers: methods for preparation of mechanochromic materialsChemical Society Reviews, 2012
- Recent advances in organic mechanofluorochromic materialsChemical Society Reviews, 2012