TY - JOUR
T1 - Competitive inclusion of molecular photo-switches in host cavities
AU - Huang, He
AU - Juan, Alberto
AU - Katsonis, Nathalie
AU - Huskens, Jurriaan
PY - 2017/8/17
Y1 - 2017/8/17
N2 - Azobenzene is a widely used guest molecule to build up dynamic photo-responsive host-guest systems. Here, we studied the host-guest complexation of a water-soluble, ortho-fluorinated azobenzene with two different host molecules, a cyclodextrin (β-CD) and a cucurbit[8]uril (CB[8]), and demonstrate that in the presence of both, the guest forms two stable supramolecular complexes selectively. In its trans-form, it favors binding to β-CD, whereas in its cis-form it favors complexation to CB[8]. Upon light-triggered photo-isomerization, the photoswitch was reversibly and selectively transferred from one host cavity to the other. This light-driven host exchange provides a new tool for supramolecular systems.
AB - Azobenzene is a widely used guest molecule to build up dynamic photo-responsive host-guest systems. Here, we studied the host-guest complexation of a water-soluble, ortho-fluorinated azobenzene with two different host molecules, a cyclodextrin (β-CD) and a cucurbit[8]uril (CB[8]), and demonstrate that in the presence of both, the guest forms two stable supramolecular complexes selectively. In its trans-form, it favors binding to β-CD, whereas in its cis-form it favors complexation to CB[8]. Upon light-triggered photo-isomerization, the photoswitch was reversibly and selectively transferred from one host cavity to the other. This light-driven host exchange provides a new tool for supramolecular systems.
KW - Dynamic molecular systems
KW - Photochromic switches
KW - Supramolecular chemistry
UR - http://www.scopus.com/inward/record.url?scp=85019434390&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2017.05.026
DO - 10.1016/j.tet.2017.05.026
M3 - Article
AN - SCOPUS:85019434390
VL - 73
SP - 4913
EP - 4917
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 33
ER -