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A Balance between van der Waals and Cation–π Interactions Stabilizes Hydrophobic Assemblies
Author(s) -
Zhan YiYang,
Kojima Tatsuo,
Koide Takuya,
Tachikawa Masanori,
Hiraoka Shuichi
Publication year - 2018
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.201801376
Subject(s) - van der waals force , substituent , benzene , chemistry , hydrophobic effect , thermal decomposition , thermal stability , ring (chemistry) , decomposition , chemical physics , computational chemistry , crystallography , molecule , stereochemistry , organic chemistry
A thermally highly stable molecular self‐assembly (nanocube) in water, the decomposition temperature of which is 415 K, was developed by designing a gear‐shaped amphiphile (GSA) with an indented hydrophobic surface, even though the nanocube is stabilized only by van der Waals (vdW) and cation–π interactions as well as the hydrophobic effect. The introduction of an electron‐donating substituent in one of the benzene rings of the GSA increased the decomposition temperature by 12 K, which is due to the stronger cation–π interactions between the benzene ring and positively charged pyridinium rings and tighter molecular meshing between the GSAs in the nanocube. The position of the substituent introduced in the benzene ring greatly affects the thermal stability of the nanocubes, and this indicates that both vdW (molecular meshing) and cation–π interactions are crucial for improving the thermal stability of the hydrophobic assemblies.