On-Surface Synthesis of Unsaturated Carbon Nanostructures with Regularly Fused Pentagon-Heptagon Pairs

被引:63
作者
Hou, Ian Cheng-Yi [1 ,5 ]
Sun, Qiang [3 ]
Eimre, Kristjan [3 ]
Di Giovannantonio, Marco [3 ]
Urgel, Jose, I [3 ]
Ruffieux, Pascal [3 ]
Narita, Akimitsu [1 ,2 ]
Fasel, Roman [3 ,4 ]
Muellen, Klaus [1 ,5 ]
机构
[1] Max Planck Inst Polymer Res, D-55128 Mainz, Germany
[2] Grad Univ, Organ & Carbon Nanomat Unit, Okinawa Inst Sci & Technol, Kunigami, Okinawa 9040495, Japan
[3] Empa, Swiss Fed Labs Mat Sci & Technol, CH-8600 Dubendorf, Switzerland
[4] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland
[5] Johannes Gutenberg Univ Mainz, Dept Chem, D-55128 Mainz, Germany
基金
瑞士国家科学基金会;
关键词
ELECTRICAL-TRANSPORT PROPERTIES; TO-NAPHTHALENE REARRANGEMENT; GRAIN-BOUNDARIES; AZULENE; GRAPHENE; DEFECTS;
D O I
10.1021/jacs.0c03635
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Multiple fused pentagon-heptagon pairs are frequently found as defects at the grain boundaries of the hexagonal graphene lattice and are suggested to have a fundamental influence on graphene-related materials. However, the construction of sp(2) carbon skeletons with multiple regularly fused pentagon-heptagon pairs is challenging. In this work, we found that the pentagon-heptagon skeleton of azulene was rearranged during the thermal reaction of an azulene-incorporated organometallic polymer on Au(111). The resulting sp(2)-carbon frameworks were characterized by high-resolution scanning probe microscopy techniques and feature novel polycyclic architectures composed of multiple regularly fused pentagon-heptagon pairs. Moreover, the calculated analysis of its aromaticity revealed a peculiar polar electronic structure.
引用
收藏
页码:10291 / 10296
页数:6
相关论文
共 60 条
[41]  
Shang J, 2015, NAT CHEM, V7, P389, DOI [10.1038/nchem.2211, 10.1038/NCHEM.2211]
[42]   Strain-induced skeletal rearrangement of a polycyclic aromatic hydrocarbon on a copper surface [J].
Shiotari, Akitoshi ;
Nakae, Takahiro ;
Iwata, Kota ;
Mori, Shigeki ;
Okujima, Tetsuo ;
Uno, Hidemitsu ;
Sakaguchi, Hiroshi ;
Sugimoto, Yoshiaki .
NATURE COMMUNICATIONS, 2017, 8
[43]   Photophysics of molecules containing multiples of the azulene carbon framework [J].
Steer, Ronald P. .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY C-PHOTOCHEMISTRY REVIEWS, 2019, 40 :68-80
[44]   Azulene-to-naphthalene rearrangement: The Car-Parrinello metadynamics method explores various mechanisms [J].
Stirling, A ;
Iannuzzi, M ;
Laio, A ;
Parrinello, M .
CHEMPHYSCHEM, 2004, 5 (10) :1558-1568
[45]   On-surface synthesis of polyazulene with 2,6-connectivity [J].
Sun, Qiang ;
Hou, Ian Cheng-Yi ;
Eimre, Kristjan ;
Pignedoli, Carlo A. ;
Ruffieux, Pascal ;
Narita, Akimitsu ;
Fasel, Roman .
CHEMICAL COMMUNICATIONS, 2019, 55 (89) :13466-13469
[46]   On-Surface Synthesis of Carbon Nanostructures [J].
Sun, Qiang ;
Zhang, Renyuan ;
Qiu, Jun ;
Liu, Rui ;
Xu, Wei .
ADVANCED MATERIALS, 2018, 30 (17)
[47]   On the reaction of azulen-2-ylmethylene(triphenyl)phosphorane.: Convenient preparation of azuleno[1,2-f]- and azuleno[1,2-A]-azulenes and their properties [J].
Takayasu, T ;
Nitta, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (23) :3537-3542
[48]   Tailoring Electrical Transport Across Grain Boundaries in Polycrystalline Graphene [J].
Tsen, Adam W. ;
Brown, Lola ;
Levendorf, Mark P. ;
Ghahari, Fereshte ;
Huang, Pinshane Y. ;
Havener, Robin W. ;
Ruiz-Vargas, Carlos S. ;
Muller, David A. ;
Kim, Philip ;
Park, Jiwoong .
SCIENCE, 2012, 336 (6085) :1143-1146
[49]   On-Surface Synthesis of Heptacene Organometallic Complexes [J].
Urgel, Jose I. ;
Hayashi, Hironobu ;
Di Giovannantonio, Marco ;
Pignedoli, Carlo A. ;
Mishra, Shantanu ;
Deniz, Okan ;
Yamashita, Masataka ;
Dienel, Thomas ;
Ruffieux, Pascal ;
Yamada, Hiroko ;
Fasel, Roman .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (34) :11658-11661
[50]   NOVEL SYNTHESIS AND MOLECULAR-STRUCTURE OF THE PYRENE ISOMER DICYCLOHEPTA[CD,GH]PENTALENE (AZULENO[2,1,8-IJA]AZULENE) [J].
VOGEL, E ;
WIELAND, H ;
SCHMALSTIEG, L ;
LEX, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (09) :717-719