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
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
收藏
页码:6320 / 6325
页数:6
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