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Materials 2016, 9(1), 48; doi:10.3390/ma9010048

Synthesis, X-ray Structure, Optical, and Electrochemical Properties of a White-Light-Emitting Molecule

Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan
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Author to whom correspondence should be addressed.
Academic Editor: Jang-Kun Song
Received: 2 December 2015 / Revised: 30 December 2015 / Accepted: 4 January 2016 / Published: 14 January 2016
(This article belongs to the Special Issue Materials for Display Applications)
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Abstract

A new white-light-emitting molecule (1) was synthesized and characterized by NMR spectroscopy, high resolution mass spectrometry, and single-crystal X-ray diffraction. Compound 1 crystallizes in the orthorhombic space group Pnma, with a = 12.6814(6), b = 7.0824(4), c = 17.4628(9) Å, α = 90°, β = 90°, γ = 90°. In the crystal, molecules are linked by weak intermolecular C-H···O hydrogen bonds, forming an infinite chain along [100], generating a C(10) motif. Compound 1 possesses an intramolecular six-membered-ring hydrogen bond, from which excited-state intramolecular proton transfer (ESIPT) takes place from the phenolic proton to the carbonyl oxygen, resulting in a tautomer that is in equilibrium with the normal species, exhibiting a dual emission that covers almost all of the visible spectrum and consequently generates white light. It exhibits one irreversible one-electron oxidation and two irreversible one-electron reductions in dichloromethane at modest potentials. Furthermore, the geometric structures, frontier molecular orbitals (MOs), and the potential energy curves (PECs) for 1 in the ground and the first singlet excited state were fully rationalized by density functional theory (DFT) and time-dependent DFT calculations. The results demonstrate that the forward and backward ESIPT may happen on a similar timescale, enabling the excited-state equilibrium to be established. View Full-Text
Keywords: ESIPT; tautomer; white-light-emitting molecules; Stokes shift; X-ray diffraction; DFT calculations ESIPT; tautomer; white-light-emitting molecules; Stokes shift; X-ray diffraction; DFT calculations
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MDPI and ACS Style

Hu, J.-W.; Wu, Y.-H.; Tsai, H.-Y.; Chen, K.-Y. Synthesis, X-ray Structure, Optical, and Electrochemical Properties of a White-Light-Emitting Molecule. Materials 2016, 9, 48.

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