Aggregation-induced emission enhancement (AIEE) of N,N '-Bis(Salicylidene)-p-Phenylenediamine Schiff base: Synthesis, photophysical properties and its DFT studies

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Publication Details

Author list: Miengmern N, Koonwong A, Sriyab S, Suramitr A, Poo-arporn RP, Hannongbua S, Suramitr S

Publisher: Elsevier

Publication year: 2019

Journal: Journal of Luminescence (0022-2313)

Volume number: 210

Start page: 493

End page: 500

Number of pages: 8

ISSN: 0022-2313

eISSN: 1872-7883

URL: https://www.sciencedirect.com/science/article/abs/pii/S0022231318314315

Languages: English-Great Britain (EN-GB)

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Abstract

The Schiff base of N,N'-Bis(Salicylidene)-p-Phenylenediamine (BSP) has been synthesized and characterized. The molecular structure and spectroscopic properties of the compound were experimentally characterized by elemental analysis, H-1 NMR, FT-IR, UV-Visible, fluorescent spectroscopic techniques, and computationally by the density functional theory (DFT) method. The appearance of photophysical properties can be ascribed to the efficiency of the excited-state intramolecular proton transfer (ESIPT) and the twisted intramolecular charge transfer (TICT) process. Their fluorescence emission performance in solution and aggregation state showed that the compound had obvious aggregation-induced emission enhancement (AIEE) characteristics, upon addition of water in acetonitrile (80:20, v/v) solution; the quantum yield (Phi(F)) is increased by 0.001-0.152. Furthermore, due to the good luminescent properties, high quantum yield and the large Stokes shifts, the compound was an ideal candidate for promising applications in metal ion sensing of Cu2+ ions.

Keywords

Aggregation-induced emission enhancement (AIEE), Density functional theory (DFT), Excited-state intramolecular proton transfer (ESIPT), Schiff base