Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks

Hui Huang, Lei Yang, Antonio Facchetti, Tobin J Marks

Research output: Contribution to journalReview article

99 Citations (Scopus)

Abstract

Constructing highly planar, extended π-electron systems is an important strategy for achieving high-mobility organic semiconductors. In general, there are two synthetic strategies for achieving π-conjugated systems with high planarity. The conventional strategy connects neighboring aromatic rings through covalent bonds to restrict the rotation about single bonds. However, this usually requires a complex sequence of synthetic steps to achieve this target, which can be costly and labor-intensive. More recently, noncovalent through-space intramolecular interactions, which are defined here as noncovalent conformational locks, have been employed with great success to increase the planarity and rigidity of extended π-electron systems; this has become a well-known and important strategy to design and synthesize highly planar π-conjugated systems for organic electronics. This review offers a comprehensive and general summary of conjugated systems with such noncovalent conformational locks, including O···S, N···S, X···S (where X = Cl, Br, F), and H···S through-space interactions, together with analysis by density functional theory computation, X-ray diffraction, and microstructural characterization, as well as by evaluation of charge transport in organic thin-film transistors and solar cells.

Original languageEnglish
Pages (from-to)10291-10318
Number of pages28
JournalChemical Reviews
Volume117
Issue number15
DOIs
Publication statusPublished - Aug 9 2017

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Semiconductor materials
Semiconducting organic compounds
Covalent bonds
Electrons
Thin film transistors
Rigidity
Density functional theory
Charge transfer
Solar cells
Electronic equipment
Personnel
X ray diffraction
single bond

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks. / Huang, Hui; Yang, Lei; Facchetti, Antonio; Marks, Tobin J.

In: Chemical Reviews, Vol. 117, No. 15, 09.08.2017, p. 10291-10318.

Research output: Contribution to journalReview article

Huang, Hui ; Yang, Lei ; Facchetti, Antonio ; Marks, Tobin J. / Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks. In: Chemical Reviews. 2017 ; Vol. 117, No. 15. pp. 10291-10318.
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