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

Patcharin Kaewmati, Yumi Yakiyama, Hiroyoshi Ohtsu, Masaki Kawano, Setsiri Haesuwannakij, Shuhei Higashibayashi, Hidehiro Sakurai

Research output: Contribution to journalArticle

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Abstract

Tris(2-hydroxyphenyl)triazasumanene ((A)-(+)-1), a bowl-shaped molecule, which possesses 2-(20-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.

Original languageEnglish
Pages (from-to)514-519
Number of pages6
JournalMaterials Chemistry Frontiers
Volume2
Issue number3
DOIs
Publication statusPublished - 2018 Jan 1

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Proton transfer
Fluorophores
Excited states
Agglomeration
Single crystals
Hexanes
Hexane
Pyridine
X ray powder diffraction
Electron microscopes
Scanning
Molecules

ASJC Scopus subject areas

  • Materials Chemistry
  • Materials Science(all)

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Tris(2-hydroxyphenyl)triazasumanene : Bowl-shaped excited-state intramolecular proton transfer (ESIPT) fluorophore coupled with aggregation-induced enhanced emission (AIEE). / Kaewmati, Patcharin; Yakiyama, Yumi; Ohtsu, Hiroyoshi; Kawano, Masaki; Haesuwannakij, Setsiri; Higashibayashi, Shuhei; Sakurai, Hidehiro.

In: Materials Chemistry Frontiers, Vol. 2, No. 3, 01.01.2018, p. 514-519.

Research output: Contribution to journalArticle

Kaewmati, Patcharin ; Yakiyama, Yumi ; Ohtsu, Hiroyoshi ; Kawano, Masaki ; Haesuwannakij, Setsiri ; Higashibayashi, Shuhei ; Sakurai, Hidehiro. / Tris(2-hydroxyphenyl)triazasumanene : Bowl-shaped excited-state intramolecular proton transfer (ESIPT) fluorophore coupled with aggregation-induced enhanced emission (AIEE). In: Materials Chemistry Frontiers. 2018 ; Vol. 2, No. 3. pp. 514-519.
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