To bend or not to bend - are heteroatom interactions within conjugated molecules effective in dictating conformation and planarity?

被引:82
作者
Conboy, Gary [1 ]
Spencer, Howard J. [2 ]
Angioni, Enrico [1 ]
Kanibolotsky, Alexander L. [1 ,3 ]
Findlay, Neil J. [1 ]
Coles, Simon J. [4 ]
Wilson, Claire [4 ]
Pitak, Mateusz B. [4 ]
Risko, Chad [5 ,6 ]
Coropceanu, Veaceslav [7 ,8 ]
Bredas, Jean-Luc [9 ]
Skabara, Peter J. [1 ]
机构
[1] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland
[2] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
[3] Inst Phys Organ Chem & Coal Chem, UA-02160 Kiev, Ukraine
[4] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England
[5] Univ Kentucky, Dept Chem, Lexington, KY 40506 USA
[6] Univ Kentucky, Ctr Appl Energy Res, Lexington, KY 40506 USA
[7] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA
[8] Georgia Inst Technol, Ctr Organ Photon & Elect, Atlanta, GA 30332 USA
[9] King Abdullah Univ Sci & Technol, Phys Sci & Engn Div, Thuwal 239556900, Saudi Arabia
基金
英国工程与自然科学研究理事会;
关键词
OPTICAL-PROPERTIES; TETRATHIAFULVALENE; POLYMERS; BONDS;
D O I
10.1039/c6mh00051g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We consider the roles of heteroatoms (mainly nitrogen, the halogens and the chalcogens) in dictating the conformation of linear conjugated molecules and polymers through non- covalent intramolecular interactions. Whilst hydrogen bonding is a competitive and sometimes more influential interaction, we provide unambiguous evidence that heteroatoms are able to determine the conformation of such materials with reasonable predictability.
引用
收藏
页码:333 / 339
页数:7
相关论文
共 24 条
  • [1] The nature of the supramolecular association of 1,2,5-chalcogenadiazoles
    Cozzolino, AF
    Vargas-Baca, I
    Mansour, S
    Mahmoudkhani, AH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) : 3184 - 3190
  • [2] Crystal Engineering: From Molecule to Crystal
    Desiraju, Gautain R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (27) : 9952 - 9967
  • [3] C-H...N and C-H...S hydrogen bonds -: Influence of hybridization on their strength
    Domagala, M
    Grabowski, SJ
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (25) : 5683 - 5688
  • [4] Salts of extended tetrathiafulvalene analogues:: relationships between molecular structure, electrochemical properties and solid state organisation
    Frère, P
    Skabara, PJ
    [J]. CHEMICAL SOCIETY REVIEWS, 2005, 34 (01) : 69 - 98
  • [5] Frisch M.J., 2016, Gaussian, V16
  • [6] Synthesis and Optical Properties of Heteroaromatic Ring Compounds Containing EDOT
    Hwang, Sun Woo
    Park, Eun Rang
    Chung, Yeon Joon
    Bae, Young Ju
    Kim, In Tae
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (07): : 2446 - 2448
  • [7] Controlling Conformations of Conjugated Polymers and Small Molecules: The Role of Nonbonding Interactions
    Jackson, Nicholas E.
    Savoie, Brett M.
    Kohlstedt, Kevin L.
    de la Cruz, Monica Olvera
    Schatz, George C.
    Chen, Lin X.
    Ratner, Mark A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (28) : 10475 - 10483
  • [8] Structural and optical properties of a thiophene-benzobisthiazole derivative
    Kang, Jun-Gill
    Cho, Hyung-Gook
    Kang, Sung Kwon
    Park, Changmoon
    Lee, Sang Woo
    Park, Gi Beum
    Lee, Jong Sook
    Kim, In Tae
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2006, 183 (1-2) : 212 - 217
  • [9] Optical and Conformational Studies on Benzobisthiazole Derivatives
    Kang, Jun-Gill
    Kim, Hyun-Joon
    Jeong, Yong-Kwang
    Nah, Min-Kook
    Park, Changmoon
    Bae, Young Ju
    Lee, Sang Woo
    Kim, In Tae
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (11) : 3791 - 3798
  • [10] Application of second-order Moller-Plesset perturbation theory with resolution-of-identity approximation to periodic systems
    Katouda, Michio
    Nagase, Shigeru
    [J]. JOURNAL OF CHEMICAL PHYSICS, 2010, 133 (18)