Synthesis and self-aggregation of cyclic alkynes containing helicene

被引：111

作者：

Nakamura, K ^{[1
]}

Okubo, H ^{[1
]}

Yamaguchi, M ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 08期

关键词：

D O I：

10.1021/ol015550w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

All stereoisomers of a cyclic alkyne containing three helicene units, 1,12-dimethylbenzo[c]phenanthrene, are synthesized using a building block. Isomeric [3 + 3]cycloalkynes aggregate in organic solvents, Vapor pressure osmometry reveals dimer formation of (M,M,M)-[3 + 3] cycloalkynes in chloroform and benzene at concentrations above 2 mM. No higher aggregation is observed. The chirality of helicenes plays an important role in self aggregation, and diastereomeric (M,P,M)-[3 + 3]cycloalkyne forms a dimer only above 15 mM. Aggregation of racemic (M*,M*,M*)-[3 + 3]cycloalkyne or (M*,P*,M*)-[3 + 3]cycloalkyne is much weaker than that of a single enantiomer.

引用

页码：1097 / 1099

页数：3

共 29 条

[1] A NEW FAMILY OF CHIRAL BINAPHTHYL-DERIVED CYCLOPHANE RECEPTORS - COMPLEXATION OF PYRANOSIDES [J].

ANDERSON, S ;

NEIDLEIN, U ;

GRAMLICH, V ;

DIEDERICH, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (15) :1596-1600

[2] Synthesis, crystal structure, and explosive decomposition of 1,2:5,6:11,12:15,16-tetrabenzo-3,7,9,13,17,19-hexadehydro[20]annulene: Formation of onion- and tube-like closed-shell carbon particles [J].

Boese, R ;

Matzger, AJ ;

Vollhardt, KPC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (08) :2052-2053

[3] Synthesis of a helical conjugated ladder polymer [J].

Dai, YJ ;

Katz, TJ ;

Nichols, DA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (18) :2109-2111

[4]

Feng P, 1998, J AM CHEM SOC, V120, P10166

[5] Synthesis of conjugated helical acetylene-bridged polymers and cyclophanes [J].

Fox, JM ;

Lin, D ;

Itagaki, Y ;

Fujita, T .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :2031-2038

[6] Versatile synthetic route to and DSC analysis of dehydrobenzoannulenes: Crystal structure of a heretofore inaccessible [20]annulene derivative [J].

Haley, MM ;

Bell, ML ;

English, JJ ;

Johnson, CA ;

Weakley, TJR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (12) :2956-2957

[7] An efficient synthesis of functionalized helicenes [J].

Katz, TJ ;

Liu, LB ;

Willmore, ND ;

Fox, JM ;

Rheingold, AL ;

Shi, SH ;

Nuckolls, C ;

Rickman, BH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (42) :10054-10063

[8] [2.2.2.2]metacyclophane-1,9,17,25-tetrayne [J].

Kawase, T ;

Ueda, N ;

Darabi, HR ;

Oda, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1556-1558

[9] Structure and morphology of helicene fibers [J].

Lovinger, AJ ;

Nuckolls, C ;

Katz, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :264-268

[10] DIOXOPORPHYRINS AS SUPRAMOLECULAR BUILDING-BLOCKS - OLIGOMER SYNTHESIS VIA PREASSEMBLY ON A LIGAND TEMPLATE [J].

MCCALLIEN, DWJ ;

SANDERS, JKM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (24) :6611-6612

← 1 2 3 →