Semiconducting nanowires from hairpin-shaped self-assembling sexithiophenes

Wei Wen Tsai, Ian D. Tevis, Alok S. Tayi, Honggang Cui, Samuel I Stupp

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

Conjugated organic molecules can be designed to self-assemble from solution into nanostructures for functions such as charge transport, light emission, or light harvesting. We report here the design and synthesis of a novel hairpin-shaped self-assembling molecule containing electronically active sexithiophene moieties. In several nonpolar organic solvents, such as toluene or chlorocyclohexane, this compound was found to form organogels composed of nanofibers with uniform diameters of 3.0 (±0.3) nm. NMR analysis and spectroscopic measurements revealed that the self-assembly is driven by π-π interactions of the sexithiophene moieties and hydrogen bonding among the amide groups at the head of the hairpin. Field effect transistors built with this molecule revealed p-type semiconducting behavior and higher hole mobilities when films were cast from solvents that promote self-assembly. We propose that hydrogen bonding and π-π stacking act synergistically to create ordered stacking of sexithiophene moieties, thus providing an efficient pathway for charge carriers within the nanowires. The nanostructures formed exhibit unusually broad absorbance in their UV-vis spectrum, which we attribute to the coexistence of both H and J aggregates from face-to-face π-π stacking of sexithiophene moieties and hierarchical bundling of the nanowires. The large absorption range associated with self-assembly of the hairpin molecules makes them potentially useful in light harvesting for energy applications.

Original languageEnglish
Pages (from-to)14778-14786
Number of pages9
JournalJournal of Physical Chemistry B
Volume114
Issue number45
DOIs
Publication statusPublished - Dec 8 2010

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assembling
Nanowires
nanowires
Self assembly
self assembly
Molecules
molecules
Nanostructures
Hydrogen bonds
Hole mobility
Light emission
hole mobility
Toluene
hydrogen
Nanofibers
Field effect transistors
Charge carriers
Amides
Organic solvents
amides

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Surfaces, Coatings and Films

Cite this

Semiconducting nanowires from hairpin-shaped self-assembling sexithiophenes. / Tsai, Wei Wen; Tevis, Ian D.; Tayi, Alok S.; Cui, Honggang; Stupp, Samuel I.

In: Journal of Physical Chemistry B, Vol. 114, No. 45, 08.12.2010, p. 14778-14786.

Research output: Contribution to journalArticle

Tsai, Wei Wen ; Tevis, Ian D. ; Tayi, Alok S. ; Cui, Honggang ; Stupp, Samuel I. / Semiconducting nanowires from hairpin-shaped self-assembling sexithiophenes. In: Journal of Physical Chemistry B. 2010 ; Vol. 114, No. 45. pp. 14778-14786.
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