Tetra-tert-butyltetraoxa[8]circulene and Its Unusual Aggregation Behaviour

被引：57

作者：

Brock-Nannestad, Theis ^{[1
]}

Nielsen, Christian B. ^{[1
]}

Schau-Magnussen, Magnus ^{[1
]}

Hammershoj, Peter ^{[1
]}

Reenberg, Theis K. ^{[1
]}

Petersen, Asger B. ^{[1
]}

Trpcevski, Denis ^{[1
]}

Pittelkow, Michael ^{[1
]}

机构：

[1] Univ Copenhagen, Dept Chem, DK-2100 Copenhagen O, Denmark

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 31期

关键词：

Supramolecular chemistry; Aggregation; Cooperative effects; Conjugation; Macrocycles; Heterocycles; CONDENSATION PRODUCTS; COMPLEX OXIDATION; PI; OLIGOMERIZATION; MACROCYCLES; QUINONES; PHENOLS; MODEL;

D O I：

10.1002/ejoc.201100966

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the first example of the synthesis of a tetraoxa[8]circulene with only four substituents by means of BF3 center dot OEt2 mediated tetramerisation of tert-butyl-1,4-benzo-quinone. Two of the four regioisomers of tetra-tert-butyltetraoxa[8]circulene have been isolated and characterised by single-crystal X-ray analysis. It was found that the tetra-tert-butyltetraoxa[8]circulenes aggregate in solution through a cooperative polymerisation mechanism despite functionalisation with bulky tert-butyl substituents.

引用

页码：6320 / 6325

页数：6

共 29 条

[21]

SCHERF U, 1992, SYNTHESIS-STUTTGART, P23

[22] LADDER POLYMERS - THE NEW GENERATION [J].

SCHLUTER, AD .

ADVANCED MATERIALS, 1991, 3 (06) :282-291

[23]

Schrader S., 1991, SYNTHETIC MET, P3223

[24] Aromatic pi-stacking in solution as revealed through the aggregation of phenylacetylene macrocycles [J].

Shetty, AS ;

Zhang, JS ;

Moore, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (05) :1019-1027

[25] How to Distinguish Isodesmic from Cooperative Supramolecular Polymerisation [J].

Smulders, Maarten M. J. ;

Nieuwenhuizen, Marko M. L. ;

de Greef, Tom F. A. ;

van der Schoot, Paul ;

Schenning, Albertus P. H. J. ;

Meijer, E. W. .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) :362-367

[26] Volumetric Properties of Binary Mixtures of 1,2-Dichloroethane with Polyethers from (283.15 to 333.15) K and at Atmospheric Pressure [J].

Valtz, Alain ;

Coquelet, Christophe ;

Boukais-Belaribi, Ghenima ;

Dahmani, Aomar ;

Belaribi, Farid Brahim .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2011, 56 (04) :1629-1657

[27] J-Aggregates: From Serendipitous Discovery to Supramolecular Engineering of Functional Dye Materials [J].

Wuerthner, Frank ;

Kaiser, Theo E. ;

Saha-Moeller, Chantu R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (15) :3376-3410

[28] NANOARCHITECTURES .3. AGGREGATION OF HEXA(PHENYLACETYLENE) MACROCYCLES IN SOLUTION - A MODEL SYSTEM FOR STUDYING PI-PI INTERACTIONS .2. [J].

ZHANG, JS ;

MOORE, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9701-9702

[29] Shape-persistent arylene ethynylene macrocycles: syntheses and supramolecular chemistry [J].

Zhao, DH ;

Moore, JS .

CHEMICAL COMMUNICATIONS, 2003, (07) :807-818

← 1 2 3 →