Palladium-Catalyzed Pentannulation of Polycyclic Aromatic Hydrocarbons

被引:56
作者
Eversloh, Christian Luetke [1 ]
Avlasevich, Yuri [1 ]
Li, Chen [1 ]
Muellen, Klaus [1 ]
机构
[1] Max Planck Inst Polymer Res, D-55128 Mainz, Germany
关键词
absorption; anthracene; cyclovoltammetry; perylene; pyrene; ORGANIC SEMICONDUCTORS; PHOTOPHYSICAL PROPERTIES; ANNULATION; EFFICIENT; TRANSPORT; HALIDES; ACENES; RING;
D O I
10.1002/chem.201101126
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We present a new and versatile one-step synthesis of a series of small molecular chromophores based on cyclopentannulated polycyclic aromatic hydrocarbons (PAH). Easily available pyrene, anthracene, and perylene bromides serve as starting materials for the reactions. The formation of the five-membered ring is achieved by the straightforward palladium(0)-catalyzed carbannulation with various substituted acetylenes. This approach is applicable either to single or multiple annulation procedures leading to hitherto inaccessible PAH topologies. According to the resulting products of the diverse reactions, a mechanistic explanation is proposed. UV/Vis absorption as well as cyclovoltammetric measurements were performed for characterization demonstrating the value of this annulation technique. Optical absorptions of up to 780 nm and absorption coefficients ranging from 8000 to 34000 m(-1)cm(-1) were detected.
引用
收藏
页码:12756 / 12762
页数:7
相关论文
共 54 条
[1]  
[Anonymous], 2010, ANGEW CHEM
[2]  
Anthony J. E., 2008, ANGEW CHEM, V120, P460
[3]   The larger acenes: Versatile organic semiconductors [J].
Anthony, John E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :452-483
[4]   FORMATION OF 6(2H)-ACEANTHRYLENONES AND THEIR PHOTOCHEMICAL CONVERSION INTO ACEANTHRYLENES [J].
BECKER, HD ;
ELEBRING, T .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1319-1322
[5]   Autocatalytic alkyne cycloadditions: Evidence for colloidal Pt catalysis [J].
Begum, RA ;
Chanda, N ;
Ramakrishna, TVV ;
Sharp, PR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) :13494-13495
[6]  
BOERE BB, 1990, RECL TRAV CHIM PAY B, V109, P463
[7]   Two-dimensional structural motif in thienoacene semiconductors: Synthesis, structure, and properties of tetrathienoanthracene isomers [J].
Brusso, Jaclyn L. ;
Hirst, Oliver D. ;
Dadvand, Afshin ;
Ganesan, Srinivasan ;
Cicoira, Fabio ;
Robertson, Craig M. ;
Oakley, Richard T. ;
Rosei, Federico ;
Perepichkat, Dmitrii F. .
CHEMISTRY OF MATERIALS, 2008, 20 (07) :2484-2494
[8]   POLYCYCLIC FLUORANTHENE HYDROCARBONS .2. A NEW GENERAL-SYNTHESIS [J].
CHO, BP ;
HARVEY, RG .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (26) :5668-5678
[9]   Charge transport in organic semiconductors [J].
Coropceanu, Veaceslav ;
Cornil, Jerome ;
da Silva Filho, Demetrio A. ;
Olivier, Yoann ;
Silbey, Robert ;
Bredas, Jean-Luc .
CHEMICAL REVIEWS, 2007, 107 (04) :926-952
[10]   One step Pd(0)-catalyzed synthesis, X-ray analysis, and photophysical properties of cyclopent[hi]aceanthrylene:: Fullerene-like properties in a nonalternant cyclopentafused aromatic hydrocarbon [J].
Dang, H ;
Levitus, M ;
Garcia-Garibay, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (01) :136-143