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Synthesis and Characterisation of Macrobicyclic Tetrathiafulvalene‐Bridged Cage Molecules
Author(s) -
Blanchard Philippe,
Svenstrup Niels,
RaultBerthelot Joëlle,
Riou Amédée,
Becher Jan
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199809)1998:9<1743::aid-ejoc1743>3.0.co;2-j
Subject(s) - tetrathiafulvalene , chemistry , cage , molecule , john cage , stereochemistry , nanotechnology , polymer chemistry , computational chemistry , organic chemistry , art history , art , materials science , mathematics , combinatorics , performance art
A series of new macrobicyclic tetrathiafulvalenophanes of type 1 and 2 with three tetrathiafulvalene bridges has been prepared under high‐dilution conditions using a stepwise selective protection‐deprotection of tetrathiafulvalenethiolates. All the macrobicyclic tetrathiafulvalenes, along with the intermediate compounds 5 and 6 and the unexpected tetrathiafulvalene pentamers 17 , were studied by cyclic voltammetry. An electrochemical investigation using the Bard‐Anson equation and thin‐layer cyclic voltammetry has been carried out, allowing an estimate of the number of electrons involved in each redox process of these multi‐redox compounds. The X‐ray crystal structure showing the unusual crystal packing of 2a is also presented.