Controlling conformations of conjugated polymers and small molecules: the role of nonbonding interactions.

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.

[1]  Mihai Irimia-Vladu,et al.  Hydrogen‐Bonded Semiconducting Pigments for Air‐Stable Field‐Effect Transistors , 2013, Advanced materials.

[2]  U. Rothlisberger,et al.  Charge transfer relaxation in donor–acceptor type conjugated materials , 2013 .

[3]  G. Bazan,et al.  Impact of regiochemistry and isoelectronic bridgehead substitution on the molecular shape and bulk organization of narrow bandgap chromophores. , 2013, Journal of the American Chemical Society.

[4]  A. Facchetti,et al.  Dialkoxybithiazole: a new building block for head-to-head polymer semiconductors. , 2013, Journal of the American Chemical Society.

[5]  S. Patil,et al.  Influence of Side-Chain on Structural Order and Photophysical Properties in Thiophene Based Diketopyrrolopyrroles: A Systematic Study , 2012 .

[6]  M. Ratner,et al.  Bithiopheneimide-dithienosilole/dithienogermole copolymers for efficient solar cells: information from structure-property-device performance correlations and comparison to thieno[3,4-c]pyrrole-4,6-dione analogues. , 2012, Journal of the American Chemical Society.

[7]  Richard A Friesner,et al.  Accurate Force Field Development for Modeling Conjugated Polymers. , 2012, Journal of chemical theory and computation.

[8]  Tomonori Kobayashi,et al.  Discovery of 3H-imidazo[4,5-c]quinolin-4(5H)-ones as potent and selective dipeptidyl peptidase IV (DPP-4) inhibitors. , 2012, Bioorganic & medicinal chemistry.

[9]  Luping Yu,et al.  Overcoming efficiency challenges in organic solar cells: rational development of conjugated polymers , 2012 .

[10]  Yong‐Young Noh,et al.  Combining electron-neutral building blocks with intramolecular "conformational locks" affords stable, high-mobility p- and n-channel polymer semiconductors. , 2012, Journal of the American Chemical Society.

[11]  Yongfang Li,et al.  Small molecule semiconductors for high-efficiency organic photovoltaics. , 2012, Chemical Society reviews.

[12]  F. Huang,et al.  Recent development of push–pull conjugated polymers for bulk-heterojunction photovoltaics: rational design and fine tailoring of molecular structures , 2012 .

[13]  Pavel Hobza,et al.  Assessment of the performance of MP2 and MP2 variants for the treatment of noncovalent interactions. , 2012, The journal of physical chemistry. A.

[14]  Daoben Zhu,et al.  Diketopyrrolopyrrole-containing quinoidal small molecules for high-performance, air-stable, and solution-processable n-channel organic field-effect transistors. , 2012, Journal of the American Chemical Society.

[15]  Yongye Liang,et al.  Ultrafast intramolecular exciton splitting dynamics in isolated low-band-gap polymers and their implications in photovoltaic materials design. , 2012, Journal of the American Chemical Society.

[16]  J. Pei,et al.  A Non‐Fullerene Small Molecule as Efficient Electron Acceptor in Organic Bulk Heterojunction Solar Cells , 2012, Advanced materials.

[17]  Lingle Wang,et al.  On achieving high accuracy and reliability in the calculation of relative protein–ligand binding affinities , 2012, Proceedings of the National Academy of Sciences.

[18]  Weitao Yang,et al.  Challenges for density functional theory. , 2012, Chemical reviews.

[19]  J. Parks,et al.  Benchmark interaction energies for biologically relevant noncovalent complexes containing divalent sulfur. , 2012, The journal of physical chemistry. A.

[20]  Yongfang Li,et al.  A D-A copolymer of dithienosilole and a new acceptor unit of naphtho[2,3-c]thiophene-4,9-dione for efficient polymer solar cells. , 2011, Chemical communications.

[21]  Yuan Zhang,et al.  A modular molecular framework for utility in small-molecule solution-processed organic photovoltaic devices , 2011 .

[22]  D. Carroll,et al.  A soluble high molecular weight copolymer of benzo[1,2-b:4,5-b']dithiophene and benzoxadiazole for efficient organic photovoltaics. , 2011, Macromolecular rapid communications.

[23]  S. Grimme,et al.  A thorough benchmark of density functional methods for general main group thermochemistry, kinetics, and noncovalent interactions. , 2011, Physical chemistry chemical physics : PCCP.

[24]  P. Frère,et al.  Facile synthesis of 3-alkoxy-4-cyanothiophenes as new building blocks for donor-acceptor conjugated systems. , 2011, Organic letters.

[25]  Jean-Philip Piquemal,et al.  NCIPLOT: a program for plotting non-covalent interaction regions. , 2011, Journal of chemical theory and computation.

[26]  Ye Tao,et al.  Bulk heterojunction solar cells using thieno[3,4-c]pyrrole-4,6-dione and dithieno[3,2-b:2',3'-d]silole copolymer with a power conversion efficiency of 7.3%. , 2011, Journal of the American Chemical Society.

[27]  B. Sumpter,et al.  Density-functional approaches to noncovalent interactions: a comparison of dispersion corrections (DFT-D), exchange-hole dipole moment (XDM) theory, and specialized functionals. , 2011, The Journal of chemical physics.

[28]  H. Sirringhaus,et al.  Thieno[3,2-b]thiophene-diketopyrrolopyrrole-containing polymers for high-performance organic field-effect transistors and organic photovoltaic devices. , 2011, Journal of the American Chemical Society.

[29]  S. Darling,et al.  Tetrathienoanthracene-based copolymers for efficient solar cells. , 2011, Journal of the American Chemical Society.

[30]  Michio Katouda,et al.  Application of second-order Møller-Plesset perturbation theory with resolution-of-identity approximation to periodic systems. , 2010, The Journal of chemical physics.

[31]  A. Doweyko,et al.  Utilization of a nitrogen-sulfur nonbonding interaction in the design of new 2-aminothiazol-5-yl-pyrimidines as p38α MAP kinase inhibitors. , 2010, Bioorganic & medicinal chemistry letters.

[32]  J. Brédas,et al.  Torsion potential in polydiacetylene: accurate computations on oligomers extrapolated to the polymer limit. , 2010, Journal of the American Chemical Society.

[33]  Gang Li,et al.  For the Bright Future—Bulk Heterojunction Polymer Solar Cells with Power Conversion Efficiency of 7.4% , 2010, Advanced materials.

[34]  Pierre M Beaujuge,et al.  Synthetic control of structural order in N-alkylthieno[3,4-c]pyrrole-4,6-dione-based polymers for efficient solar cells. , 2010, Journal of the American Chemical Society.

[35]  Yong Tian,et al.  Low-Bandgap Pyrazine Polymers: Ladder-Type Connectivity by Intramolecular S···N(sp2) Interactions and Hydrogen Bonds , 2009 .

[36]  Weitao Yang,et al.  Insights into Current Limitations of Density Functional Theory , 2008, Science.

[37]  J. Gierschner,et al.  Highly fluorinated benzobisbenzothiophenes. , 2008, Organic letters.

[38]  Sankar Subramanian,et al.  Chromophore fluorination enhances crystallization and stability of soluble anthradithiophene semiconductors. , 2008, Journal of the American Chemical Society.

[39]  Canan Atilgan,et al.  Noncovalent intramolecular interactions in the monomers and oligomers of the acceptor and donor type of low band gap conducting polymers , 2007 .

[40]  D. Truhlar,et al.  Assessment of density functionals for pi systems: Energy differences between cumulenes and poly-ynes; proton affinities, bond length alternation, and torsional potentials of conjugated polyenes; and proton affinities of conjugated Shiff bases. , 2006, The journal of physical chemistry. A.

[41]  Shawn T. Brown,et al.  Advances in methods and algorithms in a modern quantum chemistry program package. , 2006, Physical chemistry chemical physics : PCCP.

[42]  Jirí Cerný,et al.  Benchmark database of accurate (MP2 and CCSD(T) complete basis set limit) interaction energies of small model complexes, DNA base pairs, and amino acid pairs. , 2006, Physical chemistry chemical physics : PCCP.

[43]  Steve Scheiner,et al.  Relative strengths of NH..O and CH..O hydrogen bonds between polypeptide chain segments. , 2005, The journal of physical chemistry. B.

[44]  S. J. Grabowski,et al.  C-H...N and C-H...S hydrogen bonds--influence of hybridization on their strength. , 2005, The journal of physical chemistry. A.

[45]  P. Frère,et al.  3,4-Ethylenedioxythiophene (EDOT) as a versatile building block for advanced functional π-conjugated systems , 2005 .

[46]  J. Hulliger,et al.  Fluorine in crystal engineering--"the little atom that could". , 2005, Chemical Society reviews.

[47]  Interplay of Conformational States and Nonbonded Interactions in Substituted Bithiophenes , 2004 .

[48]  B. Schwartz,et al.  Conjugated polymers as molecular materials: how chain conformation and film morphology influence energy transfer and interchain interactions. , 2003, Annual review of physical chemistry.

[49]  Antonino Famulari,et al.  Computational reinvestigation of the bithiophene torsion potential , 2003 .

[50]  M. Deleuze,et al.  High level theoretical study of the structure and rotational barriers of trans-stilbene , 2003 .

[51]  A. Amarasekara,et al.  Synthesis and solid-state structures of dimethyl 2,2'-bithiophenedicarboxylates. , 2002, The Journal of organic chemistry.

[52]  Shuji Tomoda,et al.  Statistical and theoretical investigations on the directionality of nonbonded S...O interactions. Implications for molecular design and protein engineering. , 2002, Journal of the American Chemical Society.

[53]  John R. Reynolds,et al.  Low‐oxidation‐potential conducting polymers derived from 3,4‐ethylenedioxythiophene and dialkoxybenzenes , 2001 .

[54]  Steve Scheiner,et al.  Fundamental Properties of the CH···O Interaction: Is It a True Hydrogen Bond? , 1999 .

[55]  M. Pomerantz,et al.  Ester substituted bithiophenes. Abnormally low dihedral angle and rotation barrier due to dipolar stabilization , 1999 .

[56]  M. Kertész,et al.  The effects of electron correlation on the degree of bond alternation and electronic structure of oligomers of polyacetylene , 1997 .

[57]  M. Kertész,et al.  Limitations of current density functional theories for the description of partial π-bond breaking , 1997 .

[58]  Robin Taylor,et al.  Organic Fluorine Hardly Ever Accepts Hydrogen Bonds , 1997 .

[59]  W. L. Jorgensen,et al.  Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids , 1996 .

[60]  W. J. Orville-Thomas.  Atoms in Molecules — a Quantum Theory , 1996 .

[61]  Martin W. Feyereisen,et al.  Use of approximate integrals in ab initio theory. An application in MP2 energy calculations , 1993 .

[62]  Yoshiki Ogawa,et al.  Importance of an intramolecular 1,5-CH…O interaction and intermolecular interactions as factors determining conformational equilibria in 1,2-dimethoxyethane: a matrix-isolation infrared spectroscopic study , 1992 .

[63]  C. Breneman,et al.  Determining atom‐centered monopoles from molecular electrostatic potentials. The need for high sampling density in formamide conformational analysis , 1990 .

[64]  J. Ángyán,et al.  Bonding between nonbonded sulfur and oxygen atoms in selected organic molecules (a quantum chemical study) , 1987 .

[65]  S. F. Boys,et al.  The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors , 1970 .

[66]  A. Bondi.  van der Waals Volumes and Radii , 1964 .