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新型光诱导可切换β-环糊精二聚体的合成与表征。

Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer.

机构信息

Université de Picardie Jules Verne, Laboratoire de Glycochimie - Antimicrobiens et Agroressources, LG2A FRE CNRS 3517, F-80039 Amiens, France.

Université de Picardie Jules Verne, Laboratoire de Glycochimie - Antimicrobiens et Agroressources, LG2A FRE CNRS 3517, F-80039 Amiens, France ; Université d'Artois, Unité de Catalyse et de Chimie du Solide (UCCS), CNRS, UMR 8181, Rue Jean Souvraz, SP 18, F-62307 Lens, France.

出版信息

Beilstein J Org Chem. 2014 Dec 4;10:2874-85. doi: 10.3762/bjoc.10.304. eCollection 2014.

DOI:10.3762/bjoc.10.304
PMID:25550753
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4273303/
Abstract

This paper reports an efficient preparation of bridged bis-β-CD AZO-CDim 1 bearing azobenzene as a linker and exhibiting high solubility in water. The photoisomerization properties were studied by UV-vis and HPLC and supported by ab initio calculations. The cis/trans ratio of AZO-CDim 1 is 7:93 without irradiation and 37:63 after 120 min of irradiation at 365 nm; the reaction is reversible after irradiation at 254 nm. The photoinduced, switchable binding behavior of AZO-CDim 1 was evaluated by ITC, NMR and molecular modeling in the presence of a ditopic adamantyl guest. The results indicate that AZO-CDim 1 can form two different inclusion complexes with an adamantyl dimer depending on its photoinduced isomers. Both cavities of cis-AZO-CDim 1 are complexed simultaneously by two adamantyl units of the guest forming a 1:1 complex while trans-AZO-CDim 1 seems to lead to the formation of supramolecular polymers with an n:n stoichiometry.

摘要

本文报道了一种高效制备桥联双-β-CD AZO-CDim 1 的方法，该化合物以偶氮苯为连接体，在水中具有高溶解性。通过紫外可见光谱和高效液相色谱法研究了光致异构化性质，并通过从头算计算得到了支持。在 365nm 照射 120 分钟后，AZO-CDim 1 的顺式/反式比例为 37:63，而在未照射时为 7:93；在 254nm 照射后，反应是可逆的。通过 ITC、NMR 和分子模拟研究了在双位金刚烷客体存在下 AZO-CDim 1 的光诱导、可切换的结合行为。结果表明，AZO-CDim 1 可以根据其光诱导异构体与金刚烷二聚体形成两种不同的包合物。顺式-AZO-CDim 1 的两个空腔同时与客体的两个金刚烷单元络合，形成 1:1 络合物，而反式-AZO-CDim 1 似乎导致具有 n:n 化学计量比的超分子聚合物的形成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/211de1be6a05/Beilstein_J_Org_Chem-10-2874-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/c081b2570078/Beilstein_J_Org_Chem-10-2874-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/d8edbe4ec549/Beilstein_J_Org_Chem-10-2874-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/c5a40101f070/Beilstein_J_Org_Chem-10-2874-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/c10688b77114/Beilstein_J_Org_Chem-10-2874-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/579e19a867a8/Beilstein_J_Org_Chem-10-2874-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/0d8b0712b9e1/Beilstein_J_Org_Chem-10-2874-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/9db903524e06/Beilstein_J_Org_Chem-10-2874-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/df9f1a24745f/Beilstein_J_Org_Chem-10-2874-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/211de1be6a05/Beilstein_J_Org_Chem-10-2874-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/c081b2570078/Beilstein_J_Org_Chem-10-2874-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/d8edbe4ec549/Beilstein_J_Org_Chem-10-2874-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/c5a40101f070/Beilstein_J_Org_Chem-10-2874-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/c10688b77114/Beilstein_J_Org_Chem-10-2874-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/579e19a867a8/Beilstein_J_Org_Chem-10-2874-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/0d8b0712b9e1/Beilstein_J_Org_Chem-10-2874-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/9db903524e06/Beilstein_J_Org_Chem-10-2874-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/df9f1a24745f/Beilstein_J_Org_Chem-10-2874-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66e4/4273303/211de1be6a05/Beilstein_J_Org_Chem-10-2874-g009.jpg

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