Recent studies of the synthesis, functionalization, optoelectronic properties and applications of dibenzophospholes

被引:63
作者
Hibner-Kulicka, Paulina [1 ,2 ]
Joule, John Arthur [3 ]
Skalik, Joanna [1 ]
Balczewski, Piotr [1 ,4 ]
机构
[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Heteroorgan Chem, Sienkiewicza 112, PL-90363 Lodz, Poland
[2] Tech Univ Lodz, Dept Mol Phys, Zeromskiego 116, PL-90924 Lodz, Poland
[3] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
[4] Jan Dlugosz Univ Czestochowa, Inst Chem Environm Protect & Biotechnol, Fac Math & Nat Sci, Armii Krajowej 13-15, PL-42201 Czestochowa, Poland
来源
RSC ADVANCES | 2017年 / 7卷 / 15期
关键词
CONJUGATED ORGANOPHOSPHORUS MATERIALS; BUILDING-BLOCK; COMPLEXES; DERIVATIVES; PHOSPHOLES; LIGANDS; DEVICES; OXIDE; PHOSPHAFLUORENES; LUMINESCENT;
D O I
10.1039/c6ra26333j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first dibenzophospholes were described in the 1950s, but only recently have they gained greater importance, due to their use in organic electronics and the possibility of designing new p-conjugated, optoelectronic materials that incorporate these heterocycles. Our comprehensive review covering a period of 15 years (2001-2016), includes methods of synthesis of these compounds, methods for their functionalization, a description of their optoelectronic properties and their first use in optoelectronic devices. The review represents the current state of knowledge in this field and shows the great potential of simple and functionalized dibenzophospholes. The work described in this review suggests that dibenzophospholes should also be investigated more intensively as single materials, as well as in structural combinations with other p-extended conjugated aromatic and heteroaromatic systems containing phosphorus, nitrogen, silicon or sulfur atoms.
引用
收藏
页码:9194 / 9236
页数:43
相关论文
共 65 条
  • [1] IMPROVED SYNTHESES OF TETRAPHENYLPHOSPHONIUM BROMIDE AND 1-PHENYLDIBENZOPHOSPHOLE
    AFFANDI, S
    GREEN, RL
    HSIEH, BT
    HOLT, MS
    NELSON, JH
    ALYEA, EC
    [J]. SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1987, 17 (03): : 307 - 318
  • [2] Two-photon absorption properties of heterafluorenes and spirobiheterafluorenes bearing aminostyryl arms
    Agou, Tomohiro
    Hossain, Md. Delwar
    Kawashima, Takayuki
    Kamada, Kenji
    Ohta, Koji
    [J]. CHEMICAL COMMUNICATIONS, 2009, (44) : 6762 - 6764
  • [3] Slip-inversion-slip mechanism of phosphametallocene isomerization.: Spectroscopic characterization of an (η1-phospholyl)titanium complex.: Synthesis and structures of chiral mono(phospholyl)titanium complexes
    Ahn, YJ
    Rubio, RJ
    Hollis, TK
    Tham, FS
    Donnadieu, B
    [J]. ORGANOMETALLICS, 2006, 25 (05) : 1079 - 1083
  • [4] Aitken R. A., 2001, SCI SYNTH, V10, P817
  • [5] Palladium-Catalyzed Direct Synthesis of Phosphole Derivatives from Triarylphosphines through Cleavage of Carbon-Hydrogen and Carbon-Phosphorus Bonds
    Baba, Katsuaki
    Tobisu, Mamoru
    Chatani, Naoto
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (45) : 11892 - 11895
  • [6] From model compounds to extended π-conjugated systems:: Synthesis and properties of dithieno[3,2-b:2′,3′-d]phospholes
    Baumgartner, T
    Bergmans, W
    Kárpáti, T
    Neumann, T
    Nieger, M
    Nyulászi, L
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (16) : 4687 - 4699
  • [7] The dithieno[3,2-b:2′,3′-d]phosphole system:: A novel building block for highly luminescent π-conjugated materials
    Baumgartner, T
    Neumann, T
    Wirges, B
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) : 6197 - 6201
  • [8] Organophosphorus π-conjugated materials
    Baumgartner, Thomas
    Reau, Regis
    [J]. CHEMICAL REVIEWS, 2006, 106 (11) : 4681 - 4727
  • [9] Insights on the Design and Electron-Acceptor Properties of Conjugated Organophosphorus Materials
    Baumgartner, Thomas
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) : 1613 - 1622
  • [10] Dibenzophosphapentaphenes: Exploiting P Chemistry for Gap Fine-Tuning and Coordination-Driven Assembly of Planar Polycyclic Aromatic Hydrocarbons
    Bouit, Pierre-Antoine
    Escande, Aude
    Szucs, Rozsa
    Szieberth, Denes
    Lescop, Christophe
    Nyulaszi, Laszlo
    Hissler, Muriel
    Reau, Regis
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (15) : 6524 - 6527