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| rdf:type
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| Description
| - Unsubstituted 2,5-bis(2,2-bithiophene-5-yl)-1,3,4-thiadiazole and four of its derivatives containing solubilizing octyl groups in different positions of the terminal thiophene ring were synthesized. Their UV–vis absorption and emission spectra turned out to be strongly dependent on the position of the substituent and showed significant bathochromic shifts of the dominant transition for compounds with the substituents attached to Cα of the terminal ring. A good correlation was found for the experimentally determined and theoretically calculated excitation energies employing the TD CAM-B3LYP functional. The calculations showed, in addition, that the alkyl substituents improved the planarity of the molecule and its aromaticity, and that they raised the HOMO and LUMO levels via electron-donating effects. The only exception was the compound with the substituent attached to the inner Cβ position. In this case, the absorption band originating from the dominant transition was hypsochromically shifted in comparison to the corresponding transition in the unsubstituted compound, again in perfect agreement with the quantum chemical calculations, which predicted a less planar structure of this derivative. Theoretical calculations concerning the substituent-induced shifts of the HOMO and LUMO levels were found to be in good accordance with the ionization potential and the electron affinity changes determined by cyclic voltammetry, which showed the same trend. Thin films of the studied semiconductors deposited on SiO2/Si showed a highly anisotropic structure with molecules stacked almost perpendicular to the surface. Among all derivatives studied, the two compounds with substituents attached to the Cβ position formed ordered monolayers on highly oriented pyrolytic graphite in which molecular packing was much less dense than in 3D crystals. Preliminary investigations demonstrated that the synthesized new semiconductors could be used for fabrication of efficient LEDs.
- Unsubstituted 2,5-bis(2,2-bithiophene-5-yl)-1,3,4-thiadiazole and four of its derivatives containing solubilizing octyl groups in different positions of the terminal thiophene ring were synthesized. Their UV–vis absorption and emission spectra turned out to be strongly dependent on the position of the substituent and showed significant bathochromic shifts of the dominant transition for compounds with the substituents attached to Cα of the terminal ring. A good correlation was found for the experimentally determined and theoretically calculated excitation energies employing the TD CAM-B3LYP functional. The calculations showed, in addition, that the alkyl substituents improved the planarity of the molecule and its aromaticity, and that they raised the HOMO and LUMO levels via electron-donating effects. The only exception was the compound with the substituent attached to the inner Cβ position. In this case, the absorption band originating from the dominant transition was hypsochromically shifted in comparison to the corresponding transition in the unsubstituted compound, again in perfect agreement with the quantum chemical calculations, which predicted a less planar structure of this derivative. Theoretical calculations concerning the substituent-induced shifts of the HOMO and LUMO levels were found to be in good accordance with the ionization potential and the electron affinity changes determined by cyclic voltammetry, which showed the same trend. Thin films of the studied semiconductors deposited on SiO2/Si showed a highly anisotropic structure with molecules stacked almost perpendicular to the surface. Among all derivatives studied, the two compounds with substituents attached to the Cβ position formed ordered monolayers on highly oriented pyrolytic graphite in which molecular packing was much less dense than in 3D crystals. Preliminary investigations demonstrated that the synthesized new semiconductors could be used for fabrication of efficient LEDs. (en)
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| Title
| - Semiconducting alkyl derivatives of 2,5-bis(2,2'-bithiophene-5-yl)-1,3,4-thiadiazole-effect of the substituent position on the spectroscopic, electrochemical, and structural properties
- Semiconducting alkyl derivatives of 2,5-bis(2,2'-bithiophene-5-yl)-1,3,4-thiadiazole-effect of the substituent position on the spectroscopic, electrochemical, and structural properties (en)
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| skos:prefLabel
| - Semiconducting alkyl derivatives of 2,5-bis(2,2'-bithiophene-5-yl)-1,3,4-thiadiazole-effect of the substituent position on the spectroscopic, electrochemical, and structural properties
- Semiconducting alkyl derivatives of 2,5-bis(2,2'-bithiophene-5-yl)-1,3,4-thiadiazole-effect of the substituent position on the spectroscopic, electrochemical, and structural properties (en)
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| skos:notation
| - RIV/61389013:_____/13:00394402!RIV14-MSM-61389013
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| http://linked.open...avai/riv/aktivita
| |
| http://linked.open...avai/riv/aktivity
| - I, P(7E10040), P(GAP205/10/2280)
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| http://linked.open...iv/cisloPeriodika
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| http://linked.open...vai/riv/dodaniDat
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| http://linked.open...aciTvurceVysledku
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| http://linked.open.../riv/druhVysledku
| |
| http://linked.open...iv/duvernostUdaju
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| http://linked.open...titaPredkladatele
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| http://linked.open...dnocenehoVysledku
| |
| http://linked.open...ai/riv/idVysledku
| - RIV/61389013:_____/13:00394402
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| http://linked.open...riv/jazykVysledku
| |
| http://linked.open.../riv/klicovaSlova
| - thiadiazole; density functional theory; absorption spectra (en)
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| http://linked.open.../riv/klicoveSlovo
| |
| http://linked.open...odStatuVydavatele
| - US - Spojené státy americké
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| http://linked.open...ontrolniKodProRIV
| |
| http://linked.open...i/riv/nazevZdroje
| - Journal of Physical Chemistry C
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| http://linked.open...in/vavai/riv/obor
| |
| http://linked.open...ichTvurcuVysledku
| |
| http://linked.open...cetTvurcuVysledku
| |
| http://linked.open...vavai/riv/projekt
| |
| http://linked.open...UplatneniVysledku
| |
| http://linked.open...v/svazekPeriodika
| |
| http://linked.open...iv/tvurceVysledku
| - Pfleger, Jiří
- Toman, Petr
- Djurado, D.
- Nowakowski, R.
- Pron, A.
- Zagorska, M.
- Zapala, J.
- Knor, M.
- Kotwica, K.
- Kurach, E.
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| http://linked.open...ain/vavai/riv/wos
| |
| issn
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| number of pages
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| http://bibframe.org/vocab/doi
| |
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