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Crystals 2017, 7(2), 60;

Synthesis, Crystal Structure, Spectroscopic Properties, and DFT Studies of 7,9-Dibromobenzo[h]quinolin-10-ol

Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan
Department of Chemistry, Tunghai University, Taichung 40704, Taiwan
Author to whom correspondence should be addressed.
Academic Editor: Roberto Centore
Received: 9 December 2016 / Revised: 17 February 2017 / Accepted: 18 February 2017 / Published: 21 February 2017
(This article belongs to the Special Issue Polar and Centrosymmetric Packings in Molecular Crystals)
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7,9-Dibromobenzo[h]quinolin-10-ol (1), a benzo[h]quinolin-10-ol derivative, was synthesized and characterized by single-crystal X-ray diffraction. The crystal belongs to monoclinic space group P21/n, with a = 3.9573(4), b = 18.0416(18), c = 15.8210(16) Å, α = 90°, β = 96.139(3)°, and γ = 90°. Compound 1 exhibits an intramolecular six-membered-ring hydrogen bond, from which excited-state intramolecular proton transfer takes place, resulting in a proton-transfer tautomer emission of 625 nm in cyclohexane. The crystal structure is stabilized by intermolecular π–π interactions, which links a pair of molecules into a cyclic centrosymmetric dimer. Furthermore, the geometric structures, frontier molecular orbitals, and 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. View Full-Text
Keywords: 7,9-dibromobenzo[h]quinolin-10-ol; ESIPT; X-ray diffraction; DFT calculations 7,9-dibromobenzo[h]quinolin-10-ol; ESIPT; X-ray diffraction; DFT calculations

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Tsai, H.-Y.; Chang, Y.J.; Hu, J.-W.; Chen, K.-Y. Synthesis, Crystal Structure, Spectroscopic Properties, and DFT Studies of 7,9-Dibromobenzo[h]quinolin-10-ol. Crystals 2017, 7, 60.

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