Hydrogen-bonding versus .pi.-.pi. stacking in the design of organic semiconductors: from dyes to oligomers

0442968 - ÚMCH 2016 RIV NL eng J - Článek v odborném periodiku
Gospodinova, Natalia - Tomšík, Elena
Hydrogen-bonding versus .pi.-.pi. stacking in the design of organic semiconductors: from dyes to oligomers.
Progress in Polymer Science. Roč. 43, April (2015), s. 33-47. ISSN 0079-6700. E-ISSN 1873-1619
Grant CEP: GA ČR(CZ) GA13-00270S; GA ČR GPP108/11/P763
Institucionální podpora: RVO:61389013
Klíčová slova: organic semiconductors * hydrogen bonds * nematic liquid crystals
Kód oboru RIV: CD - Makromolekulární chemie
Impakt faktor: 27.184, rok: 2015

This review discusses some general aspects of the highly directional intermolecular interactions in organic solids, followed by an overview of π-conjugated systems exhibiting directional preference in the intermolecular connection and demonstrating enhanced energy and/or charge carrier transfer. As examples, “small” dyes and pigments, “intermediate-sized” N-heteroacenes, and “large” hydrogen-bonded oligomers are considered. In all of these systems the intermolecular interactions between polarized peripheries of the π-conjugated moieties ensure a preferential direction in the molecular packing. The most important among these interactions are hydrogen bonds (both strong and weak). As demonstrated recently, hydrogen bonding represents a dominant attractive force even for molecules with different polarization of the π-conjugated aromatic or heterocyclic moieties, considered to be the most favorable condition for “face-to-face” orientation (π–π stacking). The solid-state anisotropy, most likely, results from the nematic liquid-crystalline ordering of both thermotropic and lyotropic origin. Moreover, the unique efficiency of the exciton diffusion in the J-aggregates of dyes indicates significant potential of the nematic liquid-crystalline state itself for the design of organic semiconductors.
Trvalý link: http://hdl.handle.net/11104/0246515