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Synthesis of (Hemi)Carceplex Adsorbates for Self‐Assembly on Gold
Author(s) -
Huisman BartHendrik,
Rudkevich Dmitry M.,
Farrán Angeles,
Verboom Willem,
van Veggel Frank C. J. M.,
Reinhoudt David N.
Publication year - 2000
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(200001)2000:2<269::aid-ejoc269>3.0.co;2-f
Subject(s) - chemistry , monolayer , self assembly , calixarene , sulfide , crystallography , resorcinarene , self assembled monolayer , polymer chemistry , stereochemistry , nanotechnology , organic chemistry , molecule , biochemistry , materials science
The synthesis of sulfide‐functionalized (hemi)carceplexes suitable for self‐assembly on gold is described. A noncentrosymmetrical carceplex 9 (guest DMF) was synthesized by the combination of calix[4]arene 4 and resorcin[4]arene 3 , while a noncentrosymmetrical hemicarceplex 12 (guest NMP) was prepared by the combination of two different resorcin[4]arenes, 3 and 10 . These adsorbates form ordered self‐assembled monolayers on gold with their quasi C 4v axis perpendicular to the surface. The two positions possible for the incarcerated guest lead to diastereotopic surfaces.