Electron-Accepting 6,12-Diethynylindeno[1,2-b]fluorenes: Synthesis, Crystal Structures, and Photophysical Properties

被引:144
作者
Chase, Daniel T. [1 ,2 ]
Fix, Aaron G. [1 ,2 ]
Rose, Bradley D. [1 ,2 ]
Weber, Christopher D. [1 ,2 ]
Nobusue, Shunpei [1 ,2 ]
Stockwell, Chelsea E. [1 ,2 ]
Zakharov, Lev N. [1 ,2 ]
Lonergan, Mark C. [1 ,2 ]
Haley, Michael M. [1 ,2 ]
机构
[1] Univ Oregon, Dept Chem, Eugene, OR 97403 USA
[2] Univ Oregon, Inst Mat Sci, Eugene, OR 97403 USA
基金
美国国家科学基金会;
关键词
aromaticity; electron acceptors; hydrocarbons; polycycles; THIN-FILM TRANSISTORS; HIGH-PERFORMANCE; ORGANIC SEMICONDUCTORS; DERIVATIVES; DENSITY; ABSORPTION; PENTACENE; SPECTRA; ACENES; STATE;
D O I
10.1002/anie.201104797
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Acceptance is good! 2,8-Disubstituted indeno[1,2-b]fluorenes (see structure; TIPS=triisopropylsilyl) were synthesized and characterized. Electrochemical, optical, and computational data indicate that these electron-accepting hydrocarbons possess low-lying HOMO and LUMO energies, and gap energies that are comparable to common organic n-type semiconducting materials. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11103 / 11106
页数:4
相关论文
共 39 条
  • [1] STRUCTURE AND BARRIER OF INTERNAL-ROTATION OF BIPHENYL DERIVATIVES IN THE GASEOUS STATE .1. THE MOLECULAR-STRUCTURE AND NORMAL COORDINATE ANALYSIS OF NORMAL BIPHENYL AND PERDEUTERATED BIPHENYL
    ALMENNINGEN, A
    BASTIANSEN, O
    FERNHOLT, L
    CYVIN, BN
    CYVIN, SJ
    SAMDAL, S
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 1985, 128 (1-3) : 59 - 76
  • [2] Anthony J. E., 2008, ANGEW CHEM, V120, P460
  • [3] Functionalized pentacene: Improved electronic properties from control of solid-state order
    Anthony, JE
    Brooks, JS
    Eaton, DL
    Parkin, SR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) : 9482 - 9483
  • [4] A road map to stable, soluble, easily crystallized pentacene derivatives
    Anthony, JE
    Eaton, DL
    Parkin, SR
    [J]. ORGANIC LETTERS, 2002, 4 (01) : 15 - 18
  • [5] The larger acenes: Versatile organic semiconductors
    Anthony, John E.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) : 452 - 483
  • [6] Functionalized acenes and heteroacenes for organic electronics
    Anthony, John E.
    [J]. CHEMICAL REVIEWS, 2006, 106 (12) : 5028 - 5048
  • [7] Small-Molecule, Nonfullerene Acceptors for Polymer Bulk Heterojunction Organic Photovoltaics
    Anthony, John E.
    [J]. CHEMISTRY OF MATERIALS, 2011, 23 (03) : 583 - 590
  • [8] n-Type Organic Semiconductors in Organic Electronics
    Anthony, John E.
    Facchetti, Antonio
    Heeney, Martin
    Marder, Seth R.
    Zhan, Xiaowei
    [J]. ADVANCED MATERIALS, 2010, 22 (34) : 3876 - 3892
  • [9] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
    BECKE, AD
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
  • [10] Indeno[1,2-b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes
    Chase, Daniel T.
    Rose, Bradley D.
    McClintock, Sean P.
    Zakharov, Lev N.
    Haley, Michael M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) : 1127 - 1130