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Doubly Cavitand‐Capped Porphyrin Capsule by Hydrogen Bonds
Author(s) -
Kishimoto Kazuki,
Nakamura Munechika,
Kobayashi Kenji
Publication year - 2016
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.201504893
Subject(s) - cavitand , porphyrin , chemistry , hydrogen bond , solvent , photochemistry , molecule , capsule , ring (chemistry) , stereochemistry , crystallography , supramolecular chemistry , organic chemistry , botany , biology
Abstract The components of a 1:2 mixture of meso ‐tetrakis(4‐dodecyl‐3,5‐dihydroxyphenyl)porphyrin ( 1 ) and a bowl‐shaped tetrakis(4‐pyridylethynyl)cavitand ( 2 ) in CDCl 3 or C 6 D 6 self‐assemble quantitatively into the doubly cavitand‐capped porphyrin capsule 2⋅1⋅2 through eight ArOH ⋅⋅⋅ Npy hydrogen bonds. Capsule 2⋅1⋅2 possesses two cavities divided by the porphyrin ring and encapsulates two molecules of 1‐acetoxy‐3,5‐dimethoxybenzene ( G ) as a guest to form G / G @( 2⋅1⋅2 ). Remarkable solvent effect was observed, in which the apparent association constant of 2⋅1⋅2 with G in C 6 D 6 was much greater than that in CDCl 3 .