Determination of ground- and excited-state isomerization barriers for the oligothiophene 3′,4′-dibutyl-2,2′

5′,2″-terthiophene

L. DeWitt, G. J. Blanchard, E. LeGoff, M. E. Benz, J. H. Liao, Mercouri G Kanatzidis

Research output: Contribution to journalArticle

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Abstract

We report on the crystal structure and rotational isomerization of a poly(alkylthiophene) oligomer, 3′,4′-dibutyl-2,2′:5′,2″-terthiophene. The X-ray crystal structure of this polythiophene oligomer shows an all-anti configuration with an ∼ 33° mean dihedral angle between adjacent thiophene rings. Measurements of the torsional barrier to rotation between thiophene rings have been performed for both the ground and first excited singlet states of this oligomer. The So barrier to rotation is measured to be 19.7 kcal/mol using 1H NMR and the S1 barrier to rotation is determined to be 4.2 kcal/mol using fluorescence lifetime measurements. We discuss the significance of these results in the context of understanding structure/property relationships in poly(alkylthiophenes).

Original languageEnglish
Pages (from-to)12158-12164
Number of pages7
JournalJournal of the American Chemical Society
Volume115
Issue number25
Publication statusPublished - 1993

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Isomerization
Oligomers
Excited states
Ground state
Thiophenes
Thiophene
Crystal structure
Dihedral angle
Fluorescence
Nuclear magnetic resonance
X-Rays
X rays
Polymers
alpha-terthienyl

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Determination of ground- and excited-state isomerization barriers for the oligothiophene 3′,4′-dibutyl-2,2′ : 5′,2″-terthiophene. / DeWitt, L.; Blanchard, G. J.; LeGoff, E.; Benz, M. E.; Liao, J. H.; Kanatzidis, Mercouri G.

In: Journal of the American Chemical Society, Vol. 115, No. 25, 1993, p. 12158-12164.

Research output: Contribution to journalArticle

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abstract = "We report on the crystal structure and rotational isomerization of a poly(alkylthiophene) oligomer, 3′,4′-dibutyl-2,2′:5′,2″-terthiophene. The X-ray crystal structure of this polythiophene oligomer shows an all-anti configuration with an ∼ 33° mean dihedral angle between adjacent thiophene rings. Measurements of the torsional barrier to rotation between thiophene rings have been performed for both the ground and first excited singlet states of this oligomer. The So barrier to rotation is measured to be 19.7 kcal/mol using 1H NMR and the S1 barrier to rotation is determined to be 4.2 kcal/mol using fluorescence lifetime measurements. We discuss the significance of these results in the context of understanding structure/property relationships in poly(alkylthiophenes).",
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AU - Kanatzidis, Mercouri G

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N2 - We report on the crystal structure and rotational isomerization of a poly(alkylthiophene) oligomer, 3′,4′-dibutyl-2,2′:5′,2″-terthiophene. The X-ray crystal structure of this polythiophene oligomer shows an all-anti configuration with an ∼ 33° mean dihedral angle between adjacent thiophene rings. Measurements of the torsional barrier to rotation between thiophene rings have been performed for both the ground and first excited singlet states of this oligomer. The So barrier to rotation is measured to be 19.7 kcal/mol using 1H NMR and the S1 barrier to rotation is determined to be 4.2 kcal/mol using fluorescence lifetime measurements. We discuss the significance of these results in the context of understanding structure/property relationships in poly(alkylthiophenes).

AB - We report on the crystal structure and rotational isomerization of a poly(alkylthiophene) oligomer, 3′,4′-dibutyl-2,2′:5′,2″-terthiophene. The X-ray crystal structure of this polythiophene oligomer shows an all-anti configuration with an ∼ 33° mean dihedral angle between adjacent thiophene rings. Measurements of the torsional barrier to rotation between thiophene rings have been performed for both the ground and first excited singlet states of this oligomer. The So barrier to rotation is measured to be 19.7 kcal/mol using 1H NMR and the S1 barrier to rotation is determined to be 4.2 kcal/mol using fluorescence lifetime measurements. We discuss the significance of these results in the context of understanding structure/property relationships in poly(alkylthiophenes).

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