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A Flexible Cyclophane: Design, Synthesis, and Structure of a Multibridged Tris‐tetrathiafulvalene (TTF) Macrocycle
Author(s) -
Takimiya Kazuo,
Thorup Niels,
Becher Jan
Publication year - 2000
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 - 10.1002/1521-3765(20000602)6:11<1947::aid-chem1947>3.0.co;2-1
Subject(s) - tetrathiafulvalene , molecule , cyclophane , intramolecular force , chemistry , tris , chloroform , solvent , crystallization , photochemistry , stereochemistry , organic chemistry , biochemistry
The tris‐tetrathiafulvalene (TTF) macrocycles 3 with a large end‐cavity were effectively synthesized from the readily available tetrakis(cyanoethylthio)TTF by means of a selective deprotection/realkylation sequence followed by an intramolecular coupling reaction. Crystal structure analyses revealed that the neutral molecules include two ( 3 a ) or one chloroform molecule ( 3 b ) as solvent of crystallization inside the cavity, whereas the I 3 − salt of 3 b , obtained by electrocrystallization, has a molecular structure which is different from that of the neutral molecule in that the cavity has completely collapsed.