Synthesis of Mono-Functionalized Cucurbit[n]urils and Exploration of Their Applications

  • The present doctoral thesis describes the synthetic procedure of clickable mono-functionalized cucurbit[n]urils (n = 6, 7) and mainly on the exploration of new applications based on the mono-functionalized CBn. In principle, with the functionalized clickable group, various functionalized CBn derivatives can be achieved. One explored application is based on a chromophore attached to CB7 which makes the host molecule fluorescent and enables it to form a host-guest FRET pair with a corresponding fluorescent guest, which can be applied to DNA sensing. The other one is based on the functionalization of CB7 on the surface of nano-/macro-particles, thus can be applied to quantify the surface coverage densities of particles. In particular, the first part of the thesis focuses on the synthesis and characterizations of mono-functionalized CB6 and CB7, including mono-hydroxylated CB6 or CB7, propargyl attached CB6 or CB7, and fluorophore attached CB6 or CB7, and related compounds. The second part of the thesis reports a host-guest FRET pair based on the macrocyclic host CB7 labelled with carboxyfluorescein as acceptor and the nucleic stain DAPI as donor and guest. This supramolecular FRET pair is to be used for quantitative sensing of DNA with an excellent linear dependence of the ratiometric fluorescence intensities. Such approach can be applied to quantify DNA accurately and potentially be used in real-time PCR. The third part of the thesis demonstrates a strategic supramolecular application to precisely control the coverage densities on the surface of nano-/macro-particles. The key is to functionalize CB7 on the surface of particles. After that, incubation of CB7-functionalized particles application-relevant guests. In the last part, I summarize the main projects during my PhD and give the outlook about exploring more applications based on mono-functionalized CB7.

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Publishing Institution:IRC-Library, Information Resource Center der Jacobs University Bremen
Granting Institution:Jacobs Univ.
Author:Shuai Zhang
Referee:Werner Nau, Mathias Winterhalter, Uwe Pischel, Andreas Hennig
Advisor:Werner Nau
Persistent Identifier (URN):urn:nbn:de:gbv:579-opus-1008759
Document Type:PhD Thesis
Date of Successful Oral Defense:2019/06/26
Date of First Publication:2019/07/05
Academic Department:Life Sciences & Chemistry
PhD Degree:Chemistry
Focus Area:Health
Other Countries Involved:Spain
Call No:2019/6

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