Fabrication of flexible semiconductor from amphiphilic N-glycosyl napthalimides using molecular self-assembly Arun Kumar Rachamalla and Subbiah Nagarajan* 1 Department of Chemistry, National Institute of Technology Warangal, Warangal, India. E-mail: arunrachamalla47@gmail.com, snagarajan@nitw.ac.in Using natural processes as a guiding tool, scientific community is actively involved to achieve substantial advances at the interface of supramolecular chemistry and materials design. In this paper, we have synthesized a series of amphiphilic N-glycosyl naphthalimides using environmentally benign protocols in good yields. For the first time, an exclusive formation of b -anomeric product using ammonium sulfate catalyst, FDA approved GRAS chemical has been thoroughly investigated. To explore the potential of N-glycosyl naphthalimides in the field of supramolecular materials, molecular self-assembly studies were systematically performed in wide range of solvents and found to form hydrogel, orgnanogel and oleogel. The existence of molecular level interactions and assembly pattern were identified using FT-IR, NMR, SAXRD, UV-vis and Fluorescence spectral methods and proposed a suitable assembly mechanism. Morphology of supramolecular architecture with respect to the molecular structure was identified using optical microscopy and scanning electron microscopy. Rheological studies clearly disclose the strength of soft material and processability. Conductivity measurements on assembled thin films developed by drop casting of N-glycosyl naphthalimides reveals the semiconducting behaviour. Interestingly, highly flexible semiconducting material derived by anchoring of gelator on cotton fabric through hydrogen bonding displayed enhanced conducting property than the assembled thin film. The demonstrated flexible organic semiconducting material obtained via more sustainable pathway would provide an opportunity to fabricate green electronics. References 1. S. J. Danishefsky and J. R. Allen, Angew. Chemie (International Ed. English) , 2000, 39. 2. K. C. Nicolaou and H. J. Mitchell, Angew. Chemie - Int. Ed. , 2001, 40, 1576–1624. 3. B. Ernst and J. L. Magnani, Nat. Rev. Drug Discov. , 2009, 8, 661–677. 4. R. D. Astronomo and D. R. Burton, Nat. Rev. Drug Discov. , 2010, 9, 308–324. 5. M. Nishio, Phys. Chem. Chem. Phys. , 2011, 13, 13873–13900. 6. L. T. Mika, E. Cséfalvay and Á. Németh, Chem. Rev. , 2018, 118, 505–613. 7. R. M. Nelson, A. Venot, M. P. Bevilacqua, R. J. Linhardt and I. Siamenkovic, Annu. Rev. Cell Dev. Biol. , 1995, 11, 601–631. 8. B. Ernst, G. W. Hart and P. Sinay, Carbohydrates in chemistry and biology , 2008, vol. 1–4.
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