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https://hdl.handle.net/10356/94279
Title: | Spectrophotometric study of inclusion complexation of aliphatic alcohols by β-cyclodextrins with azobenzene tether | Authors: | Liu, Yu Zhao, Yanli Zhang, Heng Yi Fan, Zhi Wen, Guo Dong Ding, Fei |
Keywords: | DRNTU::Science::Chemistry::Organic chemistry::Aliphatic compounds DRNTU::Engineering::Chemical technology |
Issue Date: | 2004 | Source: | 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. | Series/Report no.: | Journal of physical chemistry B | 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. | URI: | https://hdl.handle.net/10356/94279 http://hdl.handle.net/10220/6972 |
DOI: | 10.1021/jp0380024 | Rights: | © 2004 American Chemical Society. | Fulltext Permission: | none | Fulltext Availability: | No Fulltext |
Appears in Collections: | SPMS Journal Articles |
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