Supramolecular Complexation of Biologically Important Thioflavin‐T with p‐Sulfonatocalix[4]arene

• Published in: ChemistrySelect (Weinheim) 2018-03, Vol.3 (9), p.2528-2535
• Main Authors: Saravanan, Chokalingam, Ashwin, Bosco Christin Maria Arputham, Senthilkumaran, Marimuthu, Mareeswaran, Paulpandian Muthu
• Format: Article
• Language: English
• Subjects: Cavity binding; Electrochemical analysis; p-Sulfonatocalixarene; Spectral titrations; Thioflavin T
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.201702937

The inclusion of thioflavin T (ThT) with p‐sulfonatocalix[4]arene (p‐SC4) is briefly discussed in solution as well as solid state. The restricted rotation of C−C single bond between indole and benzene ring system is the reason for emission property of ThT. The encapsulation of ThT using a flexible charged host molecule exploit the correlation between the C−C single bond rotation and emission enhancement. The binding of ThT with p‐SC4 in solution state is studied using absorption, emission, electrochemical, 1H NMR and rotating frame nuclear overhauser effect spectroscopy (ROESY) techniques. A stable water insoluble supramolecular complex is synthesized from water soluble ThT and p‐SC4. The structural features of the prepared solid complex is established from infrared (FT‐IR), powder X‐ray diffraction (XRD), Mass, 1H NMR and nuclear overhauser effect spectroscopy (NOESY) analyses. The host‐guest interaction of ThT with p‐SC4 is studied in solution as well as solid state. The photophysical properties of ThT in p‐SC4 environment is studied using optical techniques. The change of electrochemical behavior of ThT upon complexation with p‐SC4 is also analyzed. The structural features of the synthesized water insoluble complex is also well established using FT‐IR, XRD, 1H NMR and 2D NMR techniques.