mirage

Spectrophotometric study of inclusion complexation of aliphatic alcohols by β-cyclodextrins with azobenzene tether

DSpace/Manakin Repository

 

Search DR-NTU


Advanced Search Subject Search

Browse

My Account

Spectrophotometric study of inclusion complexation of aliphatic alcohols by β-cyclodextrins with azobenzene tether

Show simple item record

dc.contributor.author Liu, Yu
dc.contributor.author Zhao, Yanli
dc.contributor.author Zhang, Heng Yi
dc.contributor.author Fan, Zhi
dc.contributor.author Wen, Guo Dong
dc.contributor.author Ding, Fei
dc.date.accessioned 2011-09-05T04:09:33Z
dc.date.available 2011-09-05T04:09:33Z
dc.date.copyright 2004
dc.date.issued 2011-09-05
dc.identifier.citation Liu, Y., Zhao, Y. L., Zhang, H. Y., Fan, Z., Wen, G. D., & Ding, F. (2004). Spectrophotometric Study of Inclusion Complexation of Aliphatic Alcohols by β-Cyclodextrins with Azobenzene Tether. The Journal of Physical Chemistry B, 108(26), 8836-8843.
dc.identifier.uri http://hdl.handle.net/10220/6972
dc.description.abstract Two novel β-cyclodextrin (β -CD) derivatives possessing azobenzene functional groups as a spectral probe, i.e., mono{6-O-[4-(phenylazo)phenyl]}- β -cyclodextrin (1) and mono{6-O-[4-((4-nitrophenyl)azo)phenyl]}- β-cyclodextrin (2), were synthesized in high yields, and their complexation behaviors with aliphatic alcohols were evaluated by using UV-vis, circular dichroism, and 1H NMR spectroscopy. The induced circular dichroism (ICD) and 2D NMR spectroscopy investigations revealed that azobenzene groups attached to the β-CD rim can be deeply embedded to the β-CD cavity to form the intramolecular inclusion complexes in 10% DMSO aqueous solution. Increasing the ratio of DMSO in solution results in the gradual exclusion of the azobenzene sidearm from the β-CD cavity. Upon complexation with guest adamantanols, modified β-CD 1 or 2 displays two different binding models, that is, the competitive inclusion model for 2-adamantanol and the co-inclusion model for 1-damantanol. These two different models reasonably explain the different binding behaviors and molecular selectivities of host β-CDs toward guests. Therefore, besides acting as a spectral probe, azobenzene modified β-CDs can also effectively recognize the size/shape of guest molecules, giving good molecular selectivity up to 91 for 2-adamantanol/(+)-borneol pair by 1 and the modeate enantioselectivity (K-/K+ = 2.1) for (-)-/(+)-borneol pair by 2.
dc.format.extent 8 p.
dc.relation.ispartofseries Journal of physical chemistry B
dc.rights © 2004 American Chemical Society.
dc.subject DRNTU::Science::Chemistry::Organic chemistry::Aliphatic compounds.
dc.subject DRNTU::Engineering::Chemical technology.
dc.title Spectrophotometric study of inclusion complexation of aliphatic alcohols by β-cyclodextrins with azobenzene tether
dc.type Journal Article
dc.identifier.doi http://dx.doi.org/10.1021/jp0380024
dc.description.version None of the above
dc.identifier.rims 159672

Files in this item

Files Size Format View

There are no files associated with this item.

This item appears in the following Collection(s)

Show simple item record

Statistics

Total views

All Items Views
Spectrophotometric study of inclusion complexation of aliphatic alcohols by β-cyclodextrins with azobenzene tether 317

Total downloads

All Bitstreams Views
jp0380024.pdf 11

Top country downloads

Country Code Views
Singapore 7
United Kingdom 2

Top city downloads

city Views
Singapore 7
Southampton 2