TY - JOUR
T1 - Complexation between Pentiptycene Derived Bis(crown ther)s and CBPQT 4〈 Salt
T2 - Ion-Controlled Switchable Processes and Changeable Role of the CBPQT4〈in Host-Guest Systems
AU - Cao, Jing
AU - Guo, Jia Bin
AU - Li, Peng Fei
AU - Chen, Chuan Feng
PY - 2011/3/18
Y1 - 2011/3/18
N2 - The pentiptycene derived bis(crown ether)s with two 24- crown-8 moieties in the cis position could include the CBPQT4〈 ring inside their cavities to form 1:1 complexes, and the naphthalene groups connected in the crown ethermoieties showed less effective complexation ability toward the CBPQT4〈 ring than the host containing two terminal benzene rings. This result was probably due to the stereohindrance effect of the naphthalene groups, and it was obviously different from that of the pentiptycene derived mono(crown ether)s. For the pentiptycene derived bis(crown ether) with two 4- crown-8 moieties in the trans position, it formed a 1:2 stable complex with the CBPQT4〈 salt in solution and in the solid state, in which the pentiptycene moiety played an important role in stabilizing the complex. Moreover, binding and release of the CBPQT4〈 ring in the complexes based on the pentiptycene-derived crown ethers could be chemically controlled by adding and removing potassium ions, in which the complexation modes played the key role. Interestingly, it was further found that switching the role of the CBPQT4〈 ring in host and guest systems based on the pentiptycene derived bis(crown ether)s was easily achieved, which represents a new kind of supramolecular system.
AB - The pentiptycene derived bis(crown ether)s with two 24- crown-8 moieties in the cis position could include the CBPQT4〈 ring inside their cavities to form 1:1 complexes, and the naphthalene groups connected in the crown ethermoieties showed less effective complexation ability toward the CBPQT4〈 ring than the host containing two terminal benzene rings. This result was probably due to the stereohindrance effect of the naphthalene groups, and it was obviously different from that of the pentiptycene derived mono(crown ether)s. For the pentiptycene derived bis(crown ether) with two 4- crown-8 moieties in the trans position, it formed a 1:2 stable complex with the CBPQT4〈 salt in solution and in the solid state, in which the pentiptycene moiety played an important role in stabilizing the complex. Moreover, binding and release of the CBPQT4〈 ring in the complexes based on the pentiptycene-derived crown ethers could be chemically controlled by adding and removing potassium ions, in which the complexation modes played the key role. Interestingly, it was further found that switching the role of the CBPQT4〈 ring in host and guest systems based on the pentiptycene derived bis(crown ether)s was easily achieved, which represents a new kind of supramolecular system.
UR - http://www.scopus.com/inward/record.url?scp=79953872090&partnerID=8YFLogxK
U2 - 10.1021/jo102288r
DO - 10.1021/jo102288r
M3 - Article
AN - SCOPUS:79953872090
SN - 0022-3263
VL - 76
SP - 1644
EP - 1652
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 6
ER -