TY - JOUR
T1 - Synthesis and C70 complexation studies of a fluorescent 5,5'-bi-p-tert-butylcalix[4]arene scaffold
AU - Golan, Amos
AU - Goldberg, Israel
AU - Vigalok, Arkadi
N1 - Publisher Copyright:
© 2016 © 2016 Taylor & Francis.
PY - 2016/6/2
Y1 - 2016/6/2
N2 - In this paper, we report the synthesis and C70 complexation studies of a new fluorescent 5,5'-bi-p-tert-butylcalix[4]arene capsule with an extended hydrophobic cavity. The synthetic route required development of a series of selective protection and de-protection reactions, such as esterification and ester cleavage, as well as a cross-coupling reaction at the lower rim. The resulting 5,5'-bi-p-tert-butylcalixarene was fully characterised, including by X-ray crystallography. In the solid state, the compound exists in an open-capsule orientation, with a perfectly planar bridging biphenylene unit resulting in high fluorescence with a maximum emission peak at 390 nm. Preliminary fluorescence-based complexation experiments with C70 fullerene did not provide conclusive evidence for formation of inclusion complexes.
AB - In this paper, we report the synthesis and C70 complexation studies of a new fluorescent 5,5'-bi-p-tert-butylcalix[4]arene capsule with an extended hydrophobic cavity. The synthetic route required development of a series of selective protection and de-protection reactions, such as esterification and ester cleavage, as well as a cross-coupling reaction at the lower rim. The resulting 5,5'-bi-p-tert-butylcalixarene was fully characterised, including by X-ray crystallography. In the solid state, the compound exists in an open-capsule orientation, with a perfectly planar bridging biphenylene unit resulting in high fluorescence with a maximum emission peak at 390 nm. Preliminary fluorescence-based complexation experiments with C70 fullerene did not provide conclusive evidence for formation of inclusion complexes.
KW - C70 fullerene
KW - Calixarene capsule
KW - calixarene-fullerene complexation
KW - chemical sensors
KW - host-guest systems
UR - http://www.scopus.com/inward/record.url?scp=84954288809&partnerID=8YFLogxK
U2 - 10.1080/10610278.2015.1127374
DO - 10.1080/10610278.2015.1127374
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AN - SCOPUS:84954288809
SN - 1061-0278
VL - 28
SP - 526
EP - 535
JO - Supramolecular Chemistry
JF - Supramolecular Chemistry
IS - 5-6
ER -