Synthesis and properties of sym-pentasubstituted derivatives of corannulene

被引：79

作者：

Grube, GH ^{[1
]}

Elliott, EL ^{[1
]}

Steffens, RJ ^{[1
]}

Jones, CS ^{[1
]}

Baldridge, KK ^{[1
]}

Siegel, JS ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem, La Jolla, CA 92093 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 05期

关键词：

D O I：

10.1021/ol027565f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Alkyl, aryl, and alkynyl as well as heteroatom derivatives of sym-pentasubstituted corannulenes have been synthesized from sympentachlorocorannulene. These units form potential building blocks for future work on superstructures based on corannulene. Absorption/ emission properties follow expected trends from the parent 1. sym-Pentasubstitution gives rise to variations in the chemical dynamics of bowl inversion. van der Waals attraction is cited to explain an anomalously high barrier to bowl inversion in 10.

引用

页码：713 / 716

页数：4

共 31 条

[1]

ANET FAL, 1982, DYNAMIC NMR SPECTROS, pCH7

[2] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[3]

Buncel E, 1984, ELECT DEFICIENT AROM

[4]

CHENG PC, 1996, THESIS BOSTON COLL B, P212

[5]

Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222

[6] Investigations into the Pd-catalysed cross-coupling of phenylacetylene with aryl chlorides:: simple one-pot procedure and the effect of ZnCl2 co-catalysis [J].

Eberhard, MR ;

Wang, ZH ;

Jensen, CM .

CHEMICAL COMMUNICATIONS, 2002, (08) :818-819

[7]

Frisch M.J., 2016, Gaussian 16 Revision C. 01. 2016, V16, P01

[8]

LAMBERT JB, 1998, ORGANIC STRUCTURAL S, pCH11

[9] DEVELOPMENT OF THE COLLE-SALVETTI CORRELATION-ENERGY FORMULA INTO A FUNCTIONAL OF THE ELECTRON-DENSITY [J].

LEE, CT ;

YANG, WT ;

PARR, RG .

PHYSICAL REVIEW B, 1988, 37 (02) :785-789

[10]

Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO

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