How is the AIE mechanism profoundly changed in an ESIPT family: the novel introduction of a tetraphenylethene group onto (Z)-3-(quinolin-2-ylmethylene)-3,4-dihydroquinoxalin-2(1H)-one

Phys Chem Chem Phys. 2015 Feb 7;17(5):3287-94. doi: 10.1039/c4cp03963g. Epub 2014 Dec 19.

Abstract

It is reported that two derivatives of (Z)-3-(quinolin-2-ylmethylene)-3,4-dihydroquinoxalin-2-(1H)-one (1) with a tetraphenylethene (TPE) group introduced at amide N atom of the dihydroquinoxalinone moiety (2) or at phenyl ring of the quinoline fragment (3) are synthesized, and the derivatives exhibit a remarkably enhanced aggregation-induced emission (AIE) activity than the parent. Although both the parent and the derivatives have the characteristic of an excited state intramolecular proton transfer (ESIPT), the AIE mechanism of 2 and 3 is totally different from that of 1. The considerably stronger emission of 3 than that of 2 should be attributed to the unique crystallization-induced emission enhancement (CIEE) effect.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylene / analogs & derivatives*
  • Acetylene / chemistry
  • Crystallization
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Models, Theoretical
  • Nitrogen / chemistry
  • Quinolines / chemical synthesis
  • Quinolines / chemistry*
  • Quinoxalines / chemical synthesis
  • Quinoxalines / chemistry*
  • Spectrometry, Fluorescence
  • Thermodynamics

Substances

  • Quinolines
  • Quinoxalines
  • phenylacetylene
  • Nitrogen
  • Acetylene