Synthesis of carbohydrate based polythiophene graft poly(N,N-dimethylaminoethyl methacrylate)-co-poly(GLU-HEM) copolymer for lectin sensing

Abstract Sensing of lectins are utmost necessary for its inflammatory, digestive disorder, gut pains and toxicity to human beings and for this purpose we have chosen polythiophene (PT) for its exciting optoelectronic properties. Because of precise carbohydrate specificities of lectin and to make PT water soluble for sensing of lectin, we have synthesized polythiophene-g-poly(N,N-dimethylaminoethyl methacrylate) -co-poly(glucose-hydroxyethyl methacrylate) (PT-g-pDMAEMA-co-pGLU-HEM), [PTDG]) from polythiophene macroinitiator (PTI) by copolymerizing DMAEMA and GLU-HEM monomers mixture with CuCl/HMTETA catalyst/ligand followed by hydrolysis using alcoholic NaOMe solution. The Mn of PTI was 38000, polydispersity 2.5, head-tail (H-T) regioregularity 70 mol % and Mn of unhydrolyzed PTDG is 98,900. The UV-Vis spectra of PTDG solution shows two absorption peaks at 430 and 462 nm but it shows a sharp emission peak at 544 nm which quenches with increasing pH. Concanavalin A (ConA) shows an absorbance peak at 278 nm and with addition of PTDG solution absorbance intensity increases showing hypochromic effect. Benesi–Hildebrand plot of reciprocal molar extinction coefficients with concentration suggests 1:1 complex formation between PTDG and ConA. With addition of ConA fluorescence quenching of PTDG solution occurred and using the fluorescence intensity ratio vs concentration plot the limit of detection (LOD) of Con A lectin is found to be 57 µg/L and storing the polymer solution for two months exhibits good durability. The morphology of PTDG changes from vesicle to compound micellar aggregate on addition of Con A lectin. Graphical Abstract We have synthesized a polythiophene glcopolymer (PT-g-pDMAEMA-co-pGLU-HEM), PTDG) using ATRP technique and its UV-Vis and fluorescence spectra indicates pH responsivity and lectin sensing property with LOD of 57 µg/L.