Facile and efficient synthesis of fluorinated fullerene-fused 1,3-dioxolanes: reaction of C60 with fluorinated aromatic aldehyde mediated by lithium perchlorate

被引:5
作者
Cheng, Hao-Nan [1 ]
Zou, Yuan-Hai [1 ]
Zhang, Jian-Min [1 ,2 ]
He, Shan-Shan [1 ]
Shen, Su-Bo [1 ]
Deng, Hong-Mei [3 ]
机构
[1] Shanghai Univ, Coll Sci, Dept Chem, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[3] Shanghai Univ, Ctr Anal & Test, Shanghai 200444, Peoples R China
基金
中国国家自然科学基金;
关键词
Fullerene; Lithium perchlorate; Ionic reaction; Fluorine; Cyclic voltammetry; SOLVENT-FREE; AZOMETHINE YLIDES; HYDROXYL-GROUPS; SILYLATION; ACID;
D O I
10.1016/j.tet.2014.06.038
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of fluorinated fullerene-fused 1,3-dioxolanes have been facilely and efficiently synthesized in the presence of easily available LiClO4 center dot 3H(2)O. The influences of the number of fluoro-substituents and their positions linked to the phenyl ring on the isolated yield of fullerene-fused 1,3-dioxolanes have been studied in detail. Based on reaction facts, a possible reaction mechanism for the formation of fluorinated fullerene-fused 1,3-dioxolanes has been proposed. Furthermore, detailed ultraviolet absorption spectra, fluorescence emission spectra, and cyclic voltammogram further explain the optical properties and electronic transmission capabilities of the products. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5828 / 5833
页数:6
相关论文
共 25 条
[1]   Efficient and practical protocol for silylation of hydroxyl groups using reusable lithium perchlorate dispersed in silica gel under neutral condition [J].
Azizi, N ;
Yousefi, R ;
Saidi, MR .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (05) :817-820
[2]   Novel and efficient method for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS) under solvent-free and neutral conditions [J].
Azizi, N ;
Saidi, MR .
ORGANOMETALLICS, 2004, 23 (06) :1457-1458
[3]   LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions [J].
Azizi, N ;
Saidi, MR .
TETRAHEDRON, 2004, 60 (02) :383-387
[4]   Lithium perchlorate-catalyzed three-component coupling:: A facile and general method for the synthesis of α-aminophosphonates under solvent-free conditions [J].
Azizi, N ;
Saidi, MR .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (23) :4630-4633
[5]   Lithium perchlorate promoted highly regioselective ring opening of epoxides under solvent-free conditions [J].
Azizi, Najmodin ;
Mirmashhori, Bahareh ;
Saidi, Mohammad R. .
CATALYSIS COMMUNICATIONS, 2007, 8 (12) :2198-2203
[6]   Isolation and characterisation of C60F4, C60F6, C60F8, C60F7CF3 and C60F2O, the smallest oxahomofullerene;: the mechanism of fluorine addition to fullerenes [J].
Boltalina, OV ;
Darwish, AD ;
Street, JM ;
Taylor, R ;
Wei, XW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2002, (02) :251-256
[7]   Synthesis of Fullerene-Fused Fluorine-Containing Lactones from the Radical Reaction of [60]Fullerene with Fluorinated Phenylacetic Acids [J].
Chen, Xiaolei ;
He, Shanshan ;
Shen, Subo ;
Zhao, Jingwei ;
Zhang, Jianmin ;
Zhu, Shizheng .
SYNTHESIS-STUTTGART, 2012, 44 (15) :2347-2352
[8]   Synthesis, structure, and theoretical study of lower trifluoromethyl derivatives of [60]fullerene [J].
Dorozhkin, Evgenii I. ;
Goryunkov, Alexey A. ;
Ioffe, Ilya N. ;
Avdoshenko, Stanislav M. ;
Markov, Vitaliy Yu. ;
Tamm, Nadezhda B. ;
Ignat'eva, Daria V. ;
Sidorov, Lev N. ;
Troyanov, Sergey I. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (30) :5082-5094
[9]   New -(D-A1-D-A2)n- type conjugated polymers for photovoltaic applications: consensus between low band-gap and low HOMO energy level [J].
Hu, Xiaolian ;
Fu, Weifei ;
Zuo, Lijian ;
Shi, Hangqi ;
Chen, Meirong ;
Liu, Shiyong ;
Pan, Junying ;
Fu, Lei ;
Shi, Minmin ;
Chen, Hongzheng .
TETRAHEDRON, 2013, 69 (16) :3419-3424
[10]   Low band gap dithieno[3,2-b:2′,3′-d]silole-containing polymers, synthesis, characterization and photovoltaic application [J].
Huo, Lijun ;
Chen, Hsiang-Yu ;
Hou, Jianhui ;
Chen, Teresa L. ;
Yang, Yang .
CHEMICAL COMMUNICATIONS, 2009, (37) :5570-5572