4 years ago

Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks

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

Publisher URL: http://dx.doi.org/10.1021/acs.chemrev.7b00084

DOI: 10.1021/acs.chemrev.7b00084

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