Synthesis of Boron-Doped Polycyclic Aromatic Hydrocarbons by Tandem Intramolecular Electrophilic Arene Borylation

被引：93

作者：

Miyamoto, Fumiya ^{[1
]}

Nakatsuka, Soichiro ^{[1
]}

Yamada, Keitaro ^{[2
]}

Nakayama, Ken-ichi ^{[2
]}

Hatakeyama, Takuji ^{[1
,3
]}

机构：

[1] Kwansei Gakuin Univ, Sch Sci & Technol, Sanda, Hyogo 6691337, Japan

[2] Yamagata Univ, Grad Sch Sci & Engn, Yonezawa, Yamagata 9928510, Japan

[3] Kyoto Univ, Elements Strategy Initiat Catalysts & Batteries, Katsura, Kyoto 6158520, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

关键词：

LIGHT-EMITTING-DIODES; FIELD-EFFECT TRANSISTORS; GRAPHENE NANORIBBONS; CARBON NANOTUBES; OXYGEN REDUCTION; LOW-TEMPERATURE; M-TERPHENYLS; GROWTH; FLUORESCENCE; DERIVATIVES;

D O I：

10.1021/acs.orglett.5b03167

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tandem intramolecular electrophilic arene borylation was developed to facilitate access to B-doped polycyclic aromatic hydrocarbons (PAHs). DFT calculations revealed that electrophilic arene borylation occurred via a four-membered ring transition state, in which C-B and H-Br bonds formed in a concerted manner. An organic light-emitting diode employing the B-doped PAH as an emitter and a B-doped PAH-based field-effect transistor were successfully fabricated, demonstrating the potential of B-doped PAHs in materials science.

引用

页码：6158 / 6161

页数：4

共 57 条

[1] 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
[2] Atomically precise bottom-up fabrication of graphene nanoribbons
Cai, Jinming
Ruffieux, Pascal
Jaafar, Rached
Bieri, Marco
Braun, Thomas
Blankenburg, Stephan
Muoth, Matthias
Seitsonen, Ari P.
Saleh, Moussa
Feng, Xinliang
Muellen, Klaus
Fasel, Roman
[J]. NATURE, 2010, 466 (7305) : 470 - 473
[3] Hexathienocoronenes: Synthesis and Self-Organization
Chen, Long
Puniredd, Sreenivasa R.
Tan, Yuan-Zhi
Baumgarten, Martin
Zschieschang, Ute
Enkelmann, Volker
Pisula, Wojciech
Feng, Xinliang
Klauk, Hagen
Muellen, Klaus
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (43) : 17869 - 17872
[4] Chen YH, 2012, J MATER CHEM, V22, P18718, DOI [10.1039/c2jm32246c, 10.1039/C2JM32246C]
[5] Site-Specific Substitutional Boron Doping of Semiconducting Armchair Graphene Nanoribbons
Cloke, Ryan R.
Marangoni, Tomas
Nguyen, Giang D.
Joshi, Trinity
Rizzo, Daniel J.
Bronner, Christopher
Cao, Ting
Louie, Steven. G.
Crommie, Michael F.
Fischer, Felix R.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (28) : 8872 - 8875
[6] Superelectrophilic Intermediates in Nitrogen-Directed Aromatic Borylation
De Vries, Timothy S.
Prokofjevs, Aleksandrs
Harvey, Jeremy N.
Vedejs, Edwin
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (41) : 14679 - 14687
[7] A Boron-Containing PAH as a Substructure of Boron-Doped Graphene
Dou, Chuandong
Saito, Shohei
Matsuo, Kyohei
Hisaki, Ichiro
Yamaguchi, Shigehiro
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (49) : 12206 - 12210
[8] A ONE-POT SYNTHESIS OF M-TERPHENYLS VIA A 2-ARYNE SEQUENCE
DU, CJF
HART, H
NG, KKD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) : 3162 - 3165
[9] Strategies to Design Bipolar Small Molecules for OLEDs: Donor-Acceptor Structure and Non-Donor-Acceptor Structure
Duan, Lian
Qiao, Juan
Sun, Yongduo
Qiu, Yong
[J]. ADVANCED MATERIALS, 2011, 23 (09) : 1137 - 1144
[10] Closed network growth of fullerenes
Dunk, Paul W.
Kaiser, Nathan K.
Hendrickson, Christopher L.
Quinn, John P.
Ewels, Christopher P.
Nakanishi, Yusuke
Sasaki, Yuki
Shinohara, Hisanori
Marshall, Alan G.
Kroto, Harold W.
[J]. NATURE COMMUNICATIONS, 2012, 3

← 1 2 3 4 5 6 →