A Golden Access to Acenopentalenes

被引:23
作者
Wurm, Thomas [1 ]
Ruediger, Elias C. [1 ]
Schulmeister, Juergen [1 ]
Koser, Silke [1 ]
Rudolph, Matthias [1 ]
Rominger, Frank [1 ]
Bunz, Uwe H. F. [1 ]
Hashmi, A. Stephen K. [1 ,2 ]
机构
[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany
[2] King Abdulaziz Univ, Chem Dept, Fac Sci, Jeddah 21589, Saudi Arabia
关键词
acenes; diynes; homogeneous catalysis; materials science; pentalenes; FIELD-EFFECT TRANSISTORS; N-HETEROACENES; ORGANIC SEMICONDUCTORS; PENTALENE DERIVATIVES; CATALYZED GENERATION; VINYLIDENE COMPLEXES; PENTACENE; INSERTIONS; 1,5-DIYNES; ACETYLIDES;
D O I
10.1002/chem.201705456
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
By employing gold catalysis, starting from dialkynylated acenes a series of novel un-symmetrical aceno-annulated dibenzopentalenes has been prepared. The achieved yields range from 62-68%. The fused systems contain naphthalene, anthracene, tetracene, and pentacene units. All new compounds are soluble and stable under standard conditions. The optical properties of the systems are dominated by the dibenzopentalene core for the smaller representatives, while for the anthracene-pentacene-based aceno-benzopentalenes the optical properties of the acene group dominates. Preliminary morphology tests on thin films showed a reverse trend between crystal size and molecule size.
引用
收藏
页码:2735 / 2740
页数:6
相关论文
共 62 条
[1]  
[Anonymous], 2012, ANGEW CHEM
[2]  
Anthony J. E., 2008, ANGEW CHEM, V120, P460
[3]   Functionalized pentacene: Improved electronic properties from control of solid-state order [J].
Anthony, JE ;
Brooks, JS ;
Eaton, DL ;
Parkin, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9482-9483
[4]   The larger acenes: Versatile organic semiconductors [J].
Anthony, John E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :452-483
[5]   Functionalized acenes and heteroacenes for organic electronics [J].
Anthony, John E. .
CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048
[6]   Gold-catalysed reactions of diynes [J].
Asiri, Abdullah M. ;
Hashmi, A. Stephen K. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (16) :4471-4503
[7]  
Bucher J., 2014, ANGEW CHEM, V126, P3934
[8]   Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes [J].
Bucher, Janina ;
Wurm, Thomas ;
Taschinski, Svenja ;
Sachs, Eleni ;
Ascough, David ;
Rudolph, Matthias ;
Rominger, Frank ;
Hashmi, A. Stephen K. .
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (02) :225-233
[9]   Cyclization of Gold Acetylides: Synthesis of Vinyl Sulfonates via Gold Vinylidene Complexes [J].
Bucher, Janina ;
Wurm, Thomas ;
Nalivela, Kumara Swamy ;
Rudolph, Matthias ;
Rominger, Frank ;
Hashmi, A. Stephen K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (15) :3854-3858
[10]  
Bunz U. H. F., 2013, ANGEW CHEM, V125, P3898