Issue 3, 2018

Tris(2-hydroxyphenyl)triazasumanene: bowl-shaped excited-state intramolecular proton transfer (ESIPT) fluorophore coupled with aggregation-induced enhanced emission (AIEE)

Abstract

Tris(2-hydroxyphenyl)triazasumanene ((A)-(+)-1), a bowl-shaped molecule, which possesses 2-(2′-hydroxyphenyl)pyridine moieties, was successfully synthesised. (A)-(+)-1 showed a single peak emission in CH2Cl2, which overlapped with the emission of the triazasumanene skeleton and diminished at a high concentration, corresponding to the formation of the excited enol form. In contrast, single crystals of (A)-(+)-1 exhibited a dual emission with a large Stokes shift, indicating the presence of the excited keto form by the excited state intramolecular proton transfer (ESIPT) process. In the solution of (A)-(+)-1 containing a mixture of a large amount of a poor solvent (hexane or MeOH) and a small amount of CH2Cl2, colloidal aggregates emerged with the continuous increment of emission intensity by further addition of the poor solvent, demonstrating aggregation-induced enhanced emission (AIEE). The analysis of the morphology and the structure of the aggregates using a scanning electron microscope (SEM) and powder X-ray diffraction (PXRD) revealed the well-ordered structure of the aggregates, which possessed a molecular packing pattern similar to that of an (A)-(+)-1 single crystal.

Graphical abstract: Tris(2-hydroxyphenyl)triazasumanene: bowl-shaped excited-state intramolecular proton transfer (ESIPT) fluorophore coupled with aggregation-induced enhanced emission (AIEE)

Supplementary files

Article information

Article type
Research Article
Submitted
15 Nov 2017
Accepted
15 Jan 2018
First published
15 Jan 2018

Mater. Chem. Front., 2018,2, 514-519

Tris(2-hydroxyphenyl)triazasumanene: bowl-shaped excited-state intramolecular proton transfer (ESIPT) fluorophore coupled with aggregation-induced enhanced emission (AIEE)

P. Kaewmati, Y. Yakiyama, H. Ohtsu, M. Kawano, S. Haesuwannakij, S. Higashibayashi and H. Sakurai, Mater. Chem. Front., 2018, 2, 514 DOI: 10.1039/C7QM00530J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements