Synthesis, Crystal Structure, Spectroscopic Properties, and DFT Studies of 7,9-Dibromobenzo[h]quinolin-10-ol
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°. Compou...
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| Format: | Article |
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MDPI AG
2017-02-01
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| Series: | Crystals |
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| Online Access: | http://www.mdpi.com/2073-4352/7/2/60 |
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| author | Hsing-Yang Tsai Yuan Jay Chang Jiun-Wei Hu Kew-Yu Chen |
| author_facet | Hsing-Yang Tsai Yuan Jay Chang Jiun-Wei Hu Kew-Yu Chen |
| author_sort | Hsing-Yang Tsai |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-13T08:08:28Z |
| format | Article |
| id | doaj.art-d74d9ae341df49c7a5ee3c833c78f880 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-04-13T08:08:28Z |
| publishDate | 2017-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-d74d9ae341df49c7a5ee3c833c78f8802022-12-22T02:55:06ZengMDPI AGCrystals2073-43522017-02-01726010.3390/cryst7020060cryst7020060Synthesis, Crystal Structure, Spectroscopic Properties, and DFT Studies of 7,9-Dibromobenzo[h]quinolin-10-olHsing-Yang Tsai0Yuan Jay Chang1Jiun-Wei Hu2Kew-Yu Chen3Department of Chemical Engineering, Feng Chia University, Taichung 40724, TaiwanDepartment of Chemistry, Tunghai University, Taichung 40704, TaiwanDepartment of Chemical Engineering, Feng Chia University, Taichung 40724, TaiwanDepartment of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan7,9-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.http://www.mdpi.com/2073-4352/7/2/607,9-dibromobenzo[h]quinolin-10-olESIPTX-ray diffractionDFT calculations |
| spellingShingle | Hsing-Yang Tsai Yuan Jay Chang Jiun-Wei Hu Kew-Yu Chen Synthesis, Crystal Structure, Spectroscopic Properties, and DFT Studies of 7,9-Dibromobenzo[h]quinolin-10-ol Crystals 7,9-dibromobenzo[h]quinolin-10-ol ESIPT X-ray diffraction DFT calculations |
| title | Synthesis, Crystal Structure, Spectroscopic Properties, and DFT Studies of 7,9-Dibromobenzo[h]quinolin-10-ol |
| title_full | Synthesis, Crystal Structure, Spectroscopic Properties, and DFT Studies of 7,9-Dibromobenzo[h]quinolin-10-ol |
| title_fullStr | Synthesis, Crystal Structure, Spectroscopic Properties, and DFT Studies of 7,9-Dibromobenzo[h]quinolin-10-ol |
| title_full_unstemmed | Synthesis, Crystal Structure, Spectroscopic Properties, and DFT Studies of 7,9-Dibromobenzo[h]quinolin-10-ol |
| title_short | Synthesis, Crystal Structure, Spectroscopic Properties, and DFT Studies of 7,9-Dibromobenzo[h]quinolin-10-ol |
| title_sort | synthesis crystal structure spectroscopic properties and dft studies of 7 9 dibromobenzo h quinolin 10 ol |
| topic | 7,9-dibromobenzo[h]quinolin-10-ol ESIPT X-ray diffraction DFT calculations |
| url | http://www.mdpi.com/2073-4352/7/2/60 |
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