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J Fluoresc. 2018 Jan;28(1):13-19. doi: 10.1007/s10895-014-1425-9. Epub 2014 Aug 9.

Theoretical and Experimental Studies of N,N-Dimethyl-N'-Picryl-4,4'-Stilbenediamine.

Author information

1
School of Materials Science and Engineering, Nanyang Technological University, 50 Nanyang Avenue, Singapore, 639798, Singapore.
2
Institute of Chemistry, Humboldt University of Berlin, Berlin, Germany.
3
School of Materials Science and Engineering, Nanyang Technological University, 50 Nanyang Avenue, Singapore, 639798, Singapore. wjsteele@ntu.edu.sg.
4
Department of Biotechnology Engineering, National Institute for Biotechnology in the Negev, Ilse Kats Institute for Nanoscale Science and Technology, Ben Gurion University of the Negev, Beer Sheva, Israel.

Abstract

N,N-dimethyl-N'-picryl-4,4'-stilbenediamine (DMPSDA) was prepared, purified and crystallised in a form of black lustrous crystals, and its absorption and fluorescence spectra were recorded in cyclohexane, acetonitrile and dimethyl sulfoxide. Non-emissive intramolecular charge transfer state (ICT) was clearly observed in this molecule in all three solvents. Theoretical calculations demonstrating a betaine electronic structure of the trinitrophenyl group in the ground state of the molecule and a charge transfer nature of the long wavelength transition S0 → S1 supported the experimental observations of the ICT formation in the molecule.

KEYWORDS:

Fluorescence; Intramolecular charge transfer

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