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Synthesis of Phenylene Vinylene Macrocycles through Acyclic Diene Metathesis Macrocyclization and Their Aggregation Behavior
Author(s) -
Zhang Chenxi,
Yu Chao,
Long Hai,
Denman Ryan J.,
Jin Yinghua,
Zhang Wei
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502848
Subject(s) - phenylene , metathesis , acyclic diene metathesis , diene , chemistry , combinatorial chemistry , materials science , organic chemistry , polymer , polymerization , natural rubber
A series of phenylene vinylene macrocycles (PVMs) bearing substituents with various sizes and electronic properties have been synthesized through a one‐step acyclic diene metathesis macrocyclization approach and their aggregation behaviors have been investigated. In great contrast to the aggregation of the analogous phenylene ethynylene macrocycles, which aggregate only when substituted with electron‐withdrawing groups, these PVMs undergo exceptionally strong aggregation, regardless of the electron‐donating or ‐withdrawing characters of the substituents. The unusual aggregation behavior of the PVMs is further investigated with thermodynamic and computer modeling studies, which show a good agreement with the recently proposed direct through‐space interaction model, rather than the polar/π model. The high aggregation tendency of PVMs suggests the great potential of this novel class of shape‐persistent macrocycles in a variety of applications, such as ion channels, host–guest recognition, and catalysis.