Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 10475-10483 |
| Number of pages | 9 |
| Journal | Journal of the American Chemical Society |
| Volume | 135 |
| Issue number | 28 |
| DOIs | |
| Publication status | Published - Jul 17 2013 |
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ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Controlling conformations of conjugated polymers and small molecules : The role of nonbonding interactions. / Jackson, Nicholas E.; Savoie, Brett M.; Kohlstedt, Kevin L.; Olvera De La Cruz, Monica; Schatz, George C; Chen, Lin X.; Ratner, Mark A.
In: Journal of the American Chemical Society, Vol. 135, No. 28, 17.07.2013, p. 10475-10483.Research output: Contribution to journal › Article
}
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
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.
UR - http://www.scopus.com/inward/record.url?scp=84880377985&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84880377985&partnerID=8YFLogxK
U2 - 10.1021/ja403667s
DO - 10.1021/ja403667s
M3 - Article
C2 - 23800150
AN - SCOPUS:84880377985
VL - 135
SP - 10475
EP - 10483
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 28
ER -