Structural diversities of charge transfer organic complexes. Focus on benzenoid hydrocarbons and 7,7,8,8-tetracyanoquinodimethane

被引：57
作者：
Dobrowolski, Michal A. [1 ]
Garbarino, Gaston [2 ]
Mezouar, Mohamed [2 ]
Ciesielski, Arkadiusz [1 ,3 ]
Cyranski, Michal K. [1 ]
机构：
[1] Univ Warsaw, Fac Chem, PL-02093 Warsaw, Poland
[2] European Synchrotron Radiat Facil, F-38043 Grenoble, France
[3] Polish Acad Sci, Inst Biochem & Biophys, PL-02106 Warsaw, Poland
来源：
CRYSTENGCOMM | 2014年 / 16卷 / 03期
关键词：
MOLECULAR-STRUCTURE; PHYSICOCHEMICAL PROPERTIES; AROMATIC-HYDROCARBONS; BOND LENGTHS; CRYSTAL; SUPERCONDUCTIVITY; TCNQ; PHENANTHRENE; PICENE;
D O I：
10.1039/c3ce41703d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We have obtained three-component systems: the complexes comprising of two different benzenoid hydrocarbons together with one molecule of 7,7,8,8-tetracyanoquinodimethane (TCNQ). The X-ray single-crystal structures of naphthalene-perylene-TCNQ and pyrene-perylene-TCNQ revealed that they form face-to-face stacking between perylene and TCNQ molecules containing another hydrocarbon as a guest in the structure. We also present a pyrene-TCNQ complex with two pyrene moieties acting in similar way. In this system, charge transfer is far more efficient than in any other complexes of TCNQ with benzenoid hydrocarbons. Additionally, we have also obtained as references pyrene-TCNQ, chrysene-TCNQ, phenanthrene-TCNQ and naphthalene-TCNQ with 1 : 1 molecular ratios. These systems were also used to estimate the degrees of charge transfer.
引用
收藏
页码：415 / 429
页数：15
相关论文
共 32 条
  • [1] THEORY OF SUPERCONDUCTIVITY
    BARDEEN, J
    COOPER, LN
    SCHRIEFFER, JR
    [J]. PHYSICAL REVIEW, 1957, 108 (05): : 1175 - 1204
  • [2] MICROSCOPIC THEORY OF SUPERCONDUCTIVITY
    BARDEEN, J
    COOPER, LN
    SCHRIEFFER, JR
    [J]. PHYSICAL REVIEW, 1957, 106 (01): : 162 - 164
  • [3] Crystal growth, structure, and electronic band structure of tetracene-TCNQ
    Buurma, A. J. C.
    Jurchescu, O. D.
    Shokaryev, I.
    Baas, J.
    Meetsma, A.
    de Wijs, G. A.
    de Groot, R. A.
    Palstra, T. T. M.
    [J]. JOURNAL OF PHYSICAL CHEMISTRY C, 2007, 111 (08) : 3486 - 3489
  • [4] Structure and transport properties of the charge-transfer salt coronene - TCNQ
    Chi, X
    Besnard, C
    Thorsmolle, VK
    Butko, VY
    Taylor, AJ
    Siegrist, T
    Ramirez, AP
    [J]. CHEMISTRY OF MATERIALS, 2004, 16 (26) : 5751 - 5755
  • [5] On the aromatic stabilization of benzenoid hydrocarbons
    Ciesielski, Arkadiusz
    Stepien, Dorota K.
    Dobrowolski, Michal A.
    Dobrzycki, Lukasz
    Cyranski, Michal K.
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (81) : 10129 - 10131
  • [6] CRYSTAL-STRUCTURES OF POLYNUCLEAR AROMATIC-HYDROCARBONS - CLASSIFICATION, RATIONALIZATION AND PREDICTION FROM MOLECULAR-STRUCTURE
    DESIRAJU, GR
    GAVEZZOTTI, A
    [J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1989, 45 : 473 - 482
  • [7] Exploration of the high-pressure behaviour of polycyclic aromatic hydrocarbons: naphthalene, phenanthrene and pyrene
    Fabbiani, Francesca P. A.
    Allan, David R.
    Parsons, Simon
    Pulham, Colin R.
    [J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2006, 62 (826-842) : 826 - 842
  • [8] BOND LENGTHS AND CHARGE-TRANSFER IN TETRACYANOQUINODIMETHANE SALTS
    FLANDROIS, S
    CHASSEAU, D
    [J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1977, 33 (SEP15): : 2744 - 2750
  • [9] Herbstein F.H., 1971, Perspectives in Structural Chemistry, V4, P166
  • [10] Organic conductors:: From charge density wave TTF-TCNQ to superconducting (TMTSF)2PF6
    Jérome, D
    [J]. CHEMICAL REVIEWS, 2004, 104 (11) : 5565 - 5591
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