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

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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)

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Publication details

The article was received on 15 Nov 2017, accepted on 15 Jan 2018 and first published on 15 Jan 2018


Article type: Research Article
DOI: 10.1039/C7QM00530J
Citation: Mater. Chem. Front., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C7QM00530J

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