A divergent synthesis of 3,10-dialkylpicenes

被引:15
作者
Chen, Xi-Chao [1 ]
Nishinaga, Shuhei [1 ]
Okuda, Yasuhiro [1 ]
Zhao, Jia-Ji [1 ]
Xu, Jie [1 ]
Mori, Hiroki [1 ]
Nishihara, Yasushi [1 ,2 ]
机构
[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Earth Life & Mol Sci, Kita Ku, Okayama 7008530, Japan
[2] Japan Sci & Technol Agcy, ACT C, Kawaguchi, Saitama 3320012, Japan
来源
Organic Chemistry Frontiers | 2015年 / 2卷 / 05期
关键词
FIELD-EFFECT TRANSISTORS; CROSS-COUPLING REACTIONS; CARBON-OXYGEN BONDS; ORGANIC SEMICONDUCTORS; SUBSTITUTED PICENES; GRIGNARD-REAGENTS; HIGH-PERFORMANCE; METHYL ETHERS; THIN-FILMS; ARYL;
D O I
10.1039/c5qo00039d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 3,10-dialkylated picenes has been synthesized from 3,10-dimethoxypicene through a divergent approach involving Ni-catalyzed alkynylation of a C-O bond, alkylation, and hydrogenation.
引用
收藏
页码:536 / 541
页数:6
相关论文
共 42 条
[1]   ELECTRICAL CONDUCTIVITY OF THE PERYLENE-BROMINE COMPLEX [J].
AKAMATU, H ;
INOKUCHI, H ;
MATSUNAGA, Y .
NATURE, 1954, 173 (4395) :168-169
[2]   Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics [J].
Bendikov, M ;
Wudl, F ;
Perepichka, DF .
CHEMICAL REVIEWS, 2004, 104 (11) :4891-4945
[3]   Alkylation of 1-alkynes in THF [J].
Buck, M ;
Chong, JM .
TETRAHEDRON LETTERS, 2001, 42 (34) :5825-5827
[4]   Photoinitiated Charge Transport through π-Stacked Electron Conduits in Supramolecular Ordered Assemblies of Donor-Acceptor Triads [J].
Bullock, Joseph E. ;
Carmieli, Raanan ;
Mickley, Sarah M. ;
Vura-Weis, Josh ;
Wasielewski, Michael R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) :11919-11929
[5]   Synthesis of Substituted Picenes through Pd-Catalyzed Cross-Coupling Reaction/Annulation Sequences and Their Physicochemical Properties [J].
Chang, Ning-hui ;
Chen, Xi-chao ;
Nonobe, Hikaru ;
Okuda, Yasuhiro ;
Mori, Hiroki ;
Nakajima, Kiyohiko ;
Nishihara, Yasushi .
ORGANIC LETTERS, 2013, 15 (14) :3558-3561
[6]   Development of n-alkyl-substituted bis(pyrrolo[3,4-d])tetrathiafulvalenes as organic semiconductors for solution-processible field-effect transistors semiconductors [J].
Doi, Iori ;
Miyazaki, Eigo ;
Takimiya, Kazuo ;
Kunugi, Yoshihito .
CHEMISTRY OF MATERIALS, 2007, 19 (22) :5230-5237
[7]   Highly soluble [1]benzothieno[3,2-b]benzothiophene (BTBT) derivatives for high-performance, solution-processed organic field-effect transistors [J].
Ebata, Hideaki ;
Izawa, Takafumi ;
Miyazaki, Eigo ;
Takimiya, Kazuo ;
Ikeda, Masaaki ;
Kuwabara, Hirokazu ;
Yui, Tatsuto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (51) :15732-+
[8]   Synthesis of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophenes via cross-coupling reactions and sequential Lewis acid-catalyzed regioselective cycloaromatization of epoxide [J].
Hyodo, Keita ;
Nonobe, Hikaru ;
Nishinaga, Shuhei ;
Nishihara, Yasushi .
TETRAHEDRON LETTERS, 2014, 55 (29) :4002-4005
[9]   A NOVEL TYPE OF ORGANIC SEMICONDUCTORS - MOLECULAR FASTENER [J].
INOKUCHI, H ;
SAITO, G ;
WU, P ;
SEKI, K ;
TANG, TB ;
MORI, T ;
IMAEDA, K ;
ENOKI, T ;
HIGUCHI, Y ;
INAKA, K ;
YASUOKA, N .
CHEMISTRY LETTERS, 1986, (08) :1263-1266
[10]   Diarylrhodates as Promising Active Catalysts for the Arylation of Vinyl Ethers with Grignard Reagents [J].
Iwasaki, Takanori ;
Miyata, Yoshinori ;
Akimoto, Ryo ;
Fujli, Yuuld ;
Kuniyasu, Hitoshi ;
Kambe, Nobuaki .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (26) :9260-9263