1989
DOI: 10.1016/0379-6779(89)90661-9
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The X-ray structure and MNDO calculations of α-terthienyl: A model for polythiophenes

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Cited by 204 publications
(132 citation statements)
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“…Synthesis of T'5 3 , T'8 4 , T'11 5 , T'14 6 , and T'17 7 : We prepared all the substrates by Stille reaction of the perbromo derivatives of thiophene, 2,2'-dithiophene, 2,2':5',2''-trithiophene, 2,2':5',2'':5'',2'''-tetrathiophene, and 2,2':5',2'':5'',2''':5''',2''''-pentathiophene with commercially available 2-tributylstannylthiophene. All the products, including the unknown dodecabromo-a-tetrathiophene precursor of T'17 7 , were fully characterized by analytical and spectral data and, in the case of T'5 3 and T'8 4 , by XRD analysis (see below).…”
Section: Resultsmentioning
confidence: 99%
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“…Synthesis of T'5 3 , T'8 4 , T'11 5 , T'14 6 , and T'17 7 : We prepared all the substrates by Stille reaction of the perbromo derivatives of thiophene, 2,2'-dithiophene, 2,2':5',2''-trithiophene, 2,2':5',2'':5'',2'''-tetrathiophene, and 2,2':5',2'':5'',2''':5''',2''''-pentathiophene with commercially available 2-tributylstannylthiophene. All the products, including the unknown dodecabromo-a-tetrathiophene precursor of T'17 7 , were fully characterized by analytical and spectral data and, in the case of T'5 3 and T'8 4 , by XRD analysis (see below).…”
Section: Resultsmentioning
confidence: 99%
“…T'5 3 (70 % yield) [4] and T'8 4 (32 % yield) display sharp reversible melting points at 194 and 243 8C (differential scanning calorimetry, DSC), respectively. In the case of T'11 5 (73 % yield), T'14 6 (27 % yield), and T'17 7 (56 % yield), structural assignments and purity controls were based on NMR and mass spectrometry (MS) data.…”
Section: Resultsmentioning
confidence: 99%
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“…This is also true for MOPAC, but remember, it predicts the cc conformer as the more stable vs tt for the other calculations considered here (and all the rest except MNDO93,PM3). X-ray data of trithiophene (R3) 43 give a clear indication that the tt is the more stable, that is, this is the conformeric form in the crystal with inter-ring angles of about 6°-9°. Also, a dibutylsubstituted trithiophene has a tt configuration 44 with a higher angle of inter-ring twist than for R3 itself (not unexpected).…”
Section: Resultsmentioning
confidence: 99%
“…The results of the optimized structures revealed that the molecules have almost planar conformations, 10,30,31 and the terthienyl backbones adopt a predominately S-trans configuration analogous to α-terthiophene. 32 The dihedral angles (θ 1 ,θ 2 ) between thiophene rings and the thieno [3,4-b]pyrazine ring were (176°,176°) for both TPR1 and TPR 2 , (177°,173°) for both TPR 3 and TPR 4 , while the dihedral angle θ 3 is anti-left side with a value close to 168° for TPR 2 and 157° for both TPR 3 and TPR 4 . Examination of the non-bonded distances between sulfur and nitrogen (see Figure 3) shows that these distances (3.05 Å) are significantly shorter than the sum of the van der Waals radii of sulfur and nitrogen (3.35 Å).…”
Section: Ground State Geometriesmentioning
confidence: 99%