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Statements

Subject Item
n2:RIV%2F61389013%3A_____%2F13%3A00394402%21RIV14-MSM-61389013
rdf:type
n6:Vysledek skos:Concept
dcterms: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.
dcterms: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
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
skos:notation
RIV/61389013:_____/13:00394402!RIV14-MSM-61389013
n6:predkladatel
n10:ico%3A61389013
n3:aktivita
n16:P n16:I
n3:aktivity
I, P(7E10040), P(GAP205/10/2280)
n3:cisloPeriodika
29
n3:dodaniDat
n4:2014
n3:domaciTvurceVysledku
n13:2877139 n13:6454666
n3:druhVysledku
n18:J
n3:duvernostUdaju
n11:S
n3:entitaPredkladatele
n12:predkladatel
n3:idSjednocenehoVysledku
104612
n3:idVysledku
RIV/61389013:_____/13:00394402
n3:jazykVysledku
n17:eng
n3:klicovaSlova
thiadiazole; density functional theory; absorption spectra
n3:klicoveSlovo
n15:density%20functional%20theory n15:absorption%20spectra n15:thiadiazole
n3:kodStatuVydavatele
US - Spojené státy americké
n3:kontrolniKodProRIV
[C6C403B09740]
n3:nazevZdroje
Journal of Physical Chemistry C
n3:obor
n7:BM
n3:pocetDomacichTvurcuVysledku
2
n3:pocetTvurcuVysledku
10
n3:projekt
n14:GAP205%2F10%2F2280 n14:7E10040
n3:rokUplatneniVysledku
n4:2013
n3:svazekPeriodika
117
n3:tvurceVysledku
Kurach, E. Knor, M. Pfleger, Jiří Zapala, J. Nowakowski, R. Zagorska, M. Pron, A. Toman, Petr Djurado, D. Kotwica, K.
n3:wos
000322503600050
s:issn
1932-7447
s:numberOfPages
11
n19:doi
10.1021/jp4033832