Synthesis and Chiroptical Properties of Double-Helical (M)- and (P)-o-Oligophenylenes

被引:36
作者
Chen, Jing-Xing [1 ,2 ,3 ]
Han, Jian-Wei [1 ]
Wong, Henry N. C. [1 ,2 ,3 ,4 ,5 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China
[2] Chinese Univ Hong Kong, Shenzhen Ctr Novel Funct Mol, Shenzhen 518507, Peoples R China
[3] Chinese Univ Hong Kong, Shenzhen Res Inst, Shenzhen Municipal Key Lab Chem Synth Med Organ M, Shenzhen 518507, Peoples R China
[4] Chinese Univ Hong Kong, Ctr Novel Funct Mol, State Key Lab Synthet Chem, Dept Chem, Shatin, Hong Kong, Peoples R China
[5] Chinese Univ Hong Kong, Inst Mol Funct Mat, Shatin, Hong Kong, Peoples R China
基金
中国国家自然科学基金;
关键词
ONE HUNDRED YEARS; STEREOSELECTIVE SYNTHESES; CHIRAL TETRAPHENYLENES; MOLECULAR RECOGNITION; CHAINS; PART; CARBOHELICENES; RESOLUTION; COMPLEXES;
D O I
10.1021/acs.orglett.5b02102
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
All of the M and P isomers of optically pure oligophenylenes with 6, 8, 10, and 12 phenyl rings were synthesized and fully characterized. The Suzuki cross-coupling reaction has been revealed to be a viable strategy in the syntheses of tetraphenylene derivatives, which, together with the copper-mediated oxidative cross-coupling reaction, were employed in the quest for the oligophenylenes. X-ray diffraction analysis in combination with specific rotation and circular dichroism spectroscopy unambiguously identified the unique covalent double-helical frameworks of these oligophenylene molecules.
引用
收藏
页码:4296 / 4299
页数:4
相关论文
共 27 条
[1]   Saccharide recognition-induced transformation of pyridine-pyridone alternate oligomers from self-dimer to helical complex [J].
Abe, Hajime ;
Machiguchi, Hiroshi ;
Matsumoto, Shinya ;
Inouye, Masahiko .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4650-4661
[2]   2,3,10,11-Tetrahydroxytetraphenylene and Its Application in Molecular Recognition [J].
Cui, Jian-Fang ;
Chen, Chao ;
Gao, Xiang ;
Cai, Zong-Wei ;
Han, Jian-Wei ;
Wong, Henry N. C. .
HELVETICA CHIMICA ACTA, 2012, 95 (12) :2604-2620
[3]   A Concise Synthetic Approach Towards Hydroxytetraphenylenes [J].
Cui, Jian-Fang ;
Huang, Hui ;
Wong, Henry N. C. .
SYNLETT, 2011, (07) :1018-1022
[4]   PNA HYBRIDIZES TO COMPLEMENTARY OLIGONUCLEOTIDES OBEYING THE WATSON-CRICK HYDROGEN-BONDING RULES [J].
EGHOLM, M ;
BUCHARDT, O ;
CHRISTENSEN, L ;
BEHRENS, C ;
FREIER, SM ;
DRIVER, DA ;
BERG, RH ;
KIM, SK ;
NORDEN, B ;
NIELSEN, PE .
NATURE, 1993, 365 (6446) :566-568
[5]   One hundred years of helicene chemistry. Part 2: stereoselective syntheses and chiral separations of carbohelicenes [J].
Gingras, Marc ;
Felix, Guy ;
Peresutti, Romain .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (03) :1007-1050
[6]   One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes [J].
Gingras, Marc .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (03) :968-1006
[7]   Our Expedition in Eight-Membered Ring Compounds: From Planar Dehydrocyclooctenes to Tub-Shaped Chiral Tetraphenylenes [J].
Han, Jian-Wei ;
Li, Xin ;
Wong, Henry N. C. .
CHEMICAL RECORD, 2015, 15 (01) :107-131
[8]   Recent Developments and Applications of Chiral Tetraphenylenes [J].
Han, Jian-Wei ;
Chen, Jing-Xing ;
Li, Xin ;
Peng, Xiao-Shui ;
Wong, Henry N. C. .
SYNLETT, 2013, 24 (17) :2188-2198
[9]   Trinuclear double helicates of iron(II) and nickel(II): Self-assembly and resolution into helical enantiomers [J].
Hasenknopf, B ;
Lehn, JM .
HELVETICA CHIMICA ACTA, 1996, 79 (06) :1643-1650
[10]   THE DOUBLE-HELICAL NATURE OF THE CRYSTALLINE PART OF A-STARCH [J].
IMBERTY, A ;
CHANZY, H ;
PEREZ, S ;
BULEON, A ;
TRAN, V .
JOURNAL OF MOLECULAR BIOLOGY, 1988, 201 (02) :365-378