Layered Electron Acceptors by Dimerization of Acenes End- Capped with 1,2,5-Thiadiazoles

被引:34
|
作者
Xia, Debin [1 ]
Guo, Xin [1 ,2 ]
Chen, Long [1 ,3 ]
Baumgarten, Martin [1 ]
Keerthi, Ashok [1 ]
Muellen, Klaus [1 ]
机构
[1] Max Planck Inst Polymer Res, D-55128 Mainz, Germany
[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[3] Tianjin Univ, Sch Sci, Dept Chem, Tianjin 300072, Peoples R China
关键词
acenes; cyclization; dimerization; excimers; organic semiconductors; ORGANIC SEMICONDUCTORS; SOLAR-CELLS; INTRAMOLECULAR EXCIMER; CONJUGATED POLYMER; STATE; PHOTODIMERIZATION; FLUORESCENCE; TRANSISTORS; DEPENDENCE; PENTACENE;
D O I
10.1002/anie.201508361
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Layered electron acceptors D1-4 equipped with terminal 1,2,5-thiadiazole groups have been constructed using a one-pot protocol of acene dimerization. Their molecular structures are determined using single-crystal X-ray diffraction analysis. Photophysical and electrochemical properties of these molecules present a marked dependence on conjugation length and molecular geometry. An aggregation-induced emission peak and an intramolecular excimer emission (IEE) band were observed for D2 and D4, respectively. This work paves the way for the efficient synthesis of layered heteroacenes.
引用
收藏
页码:941 / 944
页数:4
相关论文
共 50 条
  • [21] On interaction of N-oxides of 1,2,5-thiadiazoles and 1,2,5-selenodiazoles with hydrogen peroxide and sodium hypochlorite
    Yavolovsky, AA
    Ivanov, EI
    Ivanova, RY
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2000, (11): : 1571 - 1572
  • [22] Electrochemical reduction and oxidation of 3,4-disubstituted 1,2,5-thiadiazoles
    Strunskaya, EI
    Yanilkin, VV
    Bredikhina, ZA
    Nastapova, NV
    Morozov, VI
    Maksimyuk, NI
    Sharafutdinova, DR
    Bredikhin, AA
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2003, 73 (05) : 806 - 815
  • [23] 3-HYDROXY-4-SUBSTITUTED 1,2,5-THIADIAZOLES . A NEW SYNTHESIS
    MIZSAK, SA
    PERELMAN, M
    JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (06): : 1964 - &
  • [24] CHEMISTRY OF 1,2,5-THIADIAZOLES .3. [1,2,5]THIADIAZOLO[3,4-C][1,2,5]THIADIAZOLE
    KOMIN, AP
    STREET, RW
    CARMACK, M
    JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (19): : 2749 - 2752
  • [25] Structure and stability of small nitrile sulfides and their attempted generation from 1,2,5-thiadiazoles
    Pasinszki, T
    Kárpáti, T
    Westwood, NPC
    JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (25): : 6258 - 6265
  • [26] REACTION OF 4-DIAZOINDENO [2,3-C]1,2,5-THIADIAZOLES WITH ACETYLENES
    MATAKA, S
    TAKAHASHI, K
    TASHIRO, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (APR): : 21 - 21
  • [27] STUDIES ON 10-PI-ELECTRON HETEROCYCLES CONTAINING TETRAVALENT SULFUR .2. THERMOLYSES OF STRAINED 1,2,5-OXADIAZOLES AND 1,2,5-THIADIAZOLES OF THIANORBORNANE SERIES
    TSUGE, O
    TAKATA, T
    UEDA, I
    CHEMISTRY LETTERS, 1979, (09) : 1029 - 1032
  • [28] PYRIDINE AND REDUCED PYRIDINE ANALOGS OF 1,2,5-THIADIAZOLES AS HISTAMINE H-2-RECEPTOR ANTAGONISTS
    AGRAWAL, VK
    MCNEILL, JH
    KNAUS, EE
    CLINICAL AND INVESTIGATIVE MEDICINE-MEDECINE CLINIQUE ET EXPERIMENTALE, 1987, 10 (06): : E9 - E9
  • [29] SYNTHESIS OF 1,2,5-THIADIAZOLE DERIVATIVES .2. SYNTHESIS OF 1,2,5-THIADIAZOLES FROM TETRASULPHUR TETRANITRIDE AND MONOAMINES OR VIC DIAMINES
    BERTINI, V
    DEMUNNO, A
    GAZZETTA CHIMICA ITALIANA, 1971, 101 (04): : 259 - &
  • [30] PYRIDINE AND REDUCED PYRIDINE ANALOGS OF 1,2,5-THIADIAZOLES AS HISTAMINE H-2-RECEPTOR ANTAGONISTS
    AGRAWAL, VK
    KNAUS, EE
    MCNEILL, JH
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1987, 22 (04) : 319 - 323