TY - JOUR
T1 - Controlling conformations of conjugated polymers and small molecules
T2 - The role of nonbonding interactions
AU - Jackson, Nicholas E.
AU - Savoie, Brett M.
AU - Kohlstedt, Kevin L.
AU - Olvera De La Cruz, Monica
AU - Schatz, George C.
AU - Chen, Lin X.
AU - Ratner, Mark A.
N1 - Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.
PY - 2013/7/17
Y1 - 2013/7/17
N2 - The chemical variety present in the organic electronics literature has motivated us to investigate potential nonbonding interactions often incorporated into conformational "locking" schemes. We examine a variety of potential interactions, including oxygen-sulfur, nitrogen-sulfur, and fluorine-sulfur, using accurate quantum-chemical wave function methods and noncovalent interaction (NCI) analysis on a selection of high-performing conjugated polymers and small molecules found in the literature. In addition, we evaluate a set of nonbonding interactions occurring between various heterocyclic and pendant atoms taken from a group of representative π-conjugated molecules. Together with our survey and set of interactions, it is determined that while many nonbonding interactions possess weak binding capabilities, nontraditional hydrogen-bonding interactions, oxygen-hydrogen (CH···O) and nitrogen-hydrogen (CH··· N), are alone in inducing conformational control and enhanced planarity along a polymer or small molecule backbone at room temperature.
AB - The chemical variety present in the organic electronics literature has motivated us to investigate potential nonbonding interactions often incorporated into conformational "locking" schemes. We examine a variety of potential interactions, including oxygen-sulfur, nitrogen-sulfur, and fluorine-sulfur, using accurate quantum-chemical wave function methods and noncovalent interaction (NCI) analysis on a selection of high-performing conjugated polymers and small molecules found in the literature. In addition, we evaluate a set of nonbonding interactions occurring between various heterocyclic and pendant atoms taken from a group of representative π-conjugated molecules. Together with our survey and set of interactions, it is determined that while many nonbonding interactions possess weak binding capabilities, nontraditional hydrogen-bonding interactions, oxygen-hydrogen (CH···O) and nitrogen-hydrogen (CH··· N), are alone in inducing conformational control and enhanced planarity along a polymer or small molecule backbone at room temperature.
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U2 - 10.1021/ja403667s
DO - 10.1021/ja403667s
M3 - Article
C2 - 23800150
AN - SCOPUS:84880377985
SN - 0002-7863
VL - 135
SP - 10475
EP - 10483
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 28
ER -