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Synthesis, characterization and photophysical studies of self-assembled azo biphenyl urea derivatives

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Abstract

We reported the synthesis of a new series of azobiphenyl based urea derivatives 7 and their stimulus-responsive supramolecular structures in the form of sheet like self-assembled formations. The self-assembled nanostructural formations of azo derivatives 7 are strongly dependent on the nature of the solvent present in the systems. Further, we found that the amide hydrogen played a crucial role in hydrogen bonding interactions to form a sheet like morphology upon stimulus responsive self-assembly. This was confirmed by transmission electron microscopy and atomic force microscopy.

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Notes and references

  1. L. Brunsveld, B. Folmer, E. Meijer, R. Sijbesma, Supramolecular polymers, Chem. Rev., 2001, 101, 4071–4097.

    Article  CAS  PubMed  Google Scholar 

  2. T. Aida, E. Meijer, S. Stupp, Functional supramolecular polymers, Science, 2012, 335, 813–817.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. R. R. Sinden, DNA Structure and Function, Academic Press, Inc., New York, 1994.

    Google Scholar 

  4. J. M. Lehn, Supramolecular polymer chemistry-scope and perspectives, Polym. Int., 2002, 51, 825–839.

    Article  CAS  Google Scholar 

  5. L. J. Prins, D. N. Reinhoudt, P. Timmerman, Noncovalent synthesis using hydrogen bonding, Angew. Chem., Int. Ed., 2001, 40, 2382–2426.

    Article  CAS  Google Scholar 

  6. G. A. Jeffrey, An introduction to hydrogen bonding, Oxford University Press, Oxford, 1997.

    Google Scholar 

  7. C. B. Aakeroy, K. R. Seddon, The hydrogen bond and crystal engineering, Chem. Soc. Rev., 1993, 22, 397–407.

    Article  CAS  Google Scholar 

  8. J. W. Steed and J. L. Atwood, Supramolecular Chemistry, John Wiley and Sons Ltd, Chichester, 2000.

    Google Scholar 

  9. P. S. Corbin, S. C. Zimmerman, Self-association without regard to prototropy. A heterocycle that forms extremely stable quadruply hydrogen-bonded dimers, J. Am. Chem. Soc., 1998, 120, 9710–9711.

    Article  CAS  Google Scholar 

  10. P. S. Corbin, S. C. Zimmerman, Complexation-induced unfolding of heterocyclic ureas: A hydrogen-bonded, sheet like heterodimer, J. Am. Chem. Soc., 2000, 122, 3779–3780.

    Article  CAS  Google Scholar 

  11. T. Park, S. C. Zimmerman, S. Nakashima, A highly stable quadruply hydrogen-bonded heterocomplex useful for supramolecular polymer blends, J. Am. Chem. Soc., 2005, 127, 6520–6521.

    Article  CAS  PubMed  Google Scholar 

  12. T. Park, E. M. Todd, S. Nakashima, S. C. Zimmerman, A quadruply hydrogen bonded heterocomplex displaying high-fidelity recognition, J. Am. Chem. Soc., 2005, 127, 18133–18142.

    Article  CAS  PubMed  Google Scholar 

  13. Y. Yang, J. F. Xiang, M. Xue, H. Y. Hu, C. F. Chen, Supramolecular substitution reactions between hydrazide-based molecular duplex strands: complexation induced nonsymmetry and dynamic behaviour, J. Org. Chem., 2008, 73, 6369–6377.

    Article  CAS  PubMed  Google Scholar 

  14. G. B. W. L. Ligthart, H. Ohkawa, R. P. Sijbesma, E. W. Meijer, Complementary quadruple hydrogen bonding in supramolecular copolymers, J. Am. Chem. Soc., 2005, 127, 810–811.

    Article  CAS  PubMed  Google Scholar 

  15. L. S. Shimizu, S. R. Salpage, A. A. Korous, Functional materials from self-assembled bis-urea macrocycles, Acc. Chem. Res., 2014, 47, 2116–2127.

    Article  CAS  PubMed  Google Scholar 

  16. P. Brocorens, M. Linares, C. G. Duhayon, R. Guillot, B. Andrioletti, D. Suhr, B. Isare, R. Lazzaroni, L. Bouteiller, Conformational plasticity of hydrogen bonded bis-urea supramolecular polymers, J. Phys. Chem. B, 2013, 117, 5379–5386.

    Article  CAS  PubMed  Google Scholar 

  17. K. Yabuuchi, E. M. Owusu, T. Kato, A new urea gelator: incorporation of intra-and intermolecular hydrogen bonding for stable 1D self-assembly, Org. Biomol. Chem., 2003, 1, 3464–3469.

    Article  CAS  PubMed  Google Scholar 

  18. A. Lendlein, H. Jiang, O. Junger, R. Langer, Light-induced shape-memory polymers, Nature, 2005, 434, 879–882.

    Article  CAS  PubMed  Google Scholar 

  19. J. Lee, C. Y. Koh, J. P. Singer, S. Jeon, M. Maldovan, O. Stein, E. L. Thomas, 25th anniversary article: ordered polymer structures for the engineering of photons and phonons, Adv. Mater., 2014, 26, 532–569.

    Article  CAS  PubMed  Google Scholar 

  20. S. Yagai, M. Yamauchi, A. Kobayashi, T. Karatsu, A. Kitamura, T. Ohba, Y. Kikkawa, Control over hierarchy levels in the self-assembly of stackable nanotoroids, J. Am. Chem. Soc., 2012, 134, 18205–18208.

    Article  CAS  PubMed  Google Scholar 

  21. V. Balzani, M. C. Leon, A. Credi, B. Ferrer, M. Venturi, A. H. Flood, J. F. Stoddart, Proc. Natl. Acad. Sci. U. S. A., 2006, 103, 1178–1183.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. H. M. D. Bandara, S. C. Burdette, Photoisomerization in different classes of azobenzene, Chem. Soc. Rev., 2012, 41, 1809–1825.

    Article  CAS  PubMed  Google Scholar 

  23. S. Dawn, M. B. Dewal, D. Sobransingh, M. C. Paderes, A. C. Wibowo, M. D. Smith, J. A. Krause, P. J. Pellechia, L. S. Shimizu, Self-assembled phenylethynylene bis-urea macrocycles facilitate the selective photodimerization of coumarin, J. Am. Chem. Soc., 2011, 133, 7025–7032.

    Article  CAS  PubMed  Google Scholar 

  24. Y. C. Wang, J. Wu, Y. Li, J. Z. Du, Y. Y. Yuan, J. Wang, Engineering nanoscopic hydrogels via photo-crosslinking salt-induced polymer assembly for targeted drug delivery, Chem. Commun., 2010, 46, 3520–3522.

    Article  CAS  Google Scholar 

  25. J. Gao, Y. He, H. Xu, B. Song, X. Zhang, Z. Wang, X. Wang, Azobenzene-containing supramolecular polymer films for laser-induced surface relief gratings, Chem. Mater., 2007, 19, 14–17.

    Article  CAS  Google Scholar 

  26. J. Gao, Y. He, F. Liu, X. Zhang, Z. Wang, X. Wang, Azobenzene-containing supramolecular side-chain polymer films for laser-induced surface relief gratings, Chem. Mater., 2007, 19, 3877–3881.

    Article  CAS  Google Scholar 

  27. D. Gust, J. Andreasson, U. Pischel, T. A. Moore, A. L. Moore, Data and signal processing using photochromic molecules, Chem. Commun., 2012, 48, 1947–1957.

    Article  CAS  Google Scholar 

  28. X. Liang, X. Yue, Z. Dai, J. I. Kikuchi, Photoresponsive liposomal nanohybrid cerasomes, Chem. Commun., 2011, 47, 4751–7453.

    Article  CAS  Google Scholar 

  29. Z. Yu, S. Hecht, Reversible and quantitative denaturation of amphiphilic oligo(azobenzene) foldamers, Angew. Chem., Int. Ed., 2011, 50, 1640–1643.

    Article  CAS  Google Scholar 

  30. I. Willerich, F. Grohn, Photoswitchable nanoassemblies by electrostatic self-assembly, Angew. Chem., Int. Ed., 2010, 49, 8104–8108.

    Article  CAS  Google Scholar 

  31. O. Yaroshchuk, Y. Reznikov, Photoalignment of liquid crystals: basics and current trends, J. Mater. Chem., 2012, 22, 286–300.

    Article  CAS  Google Scholar 

  32. W. Wu, L. Yao, T. Yang, R. Yin, F. Li, Y. Yu, NIR-light-induced deformation of cross-linked liquid-crystal polymers using upconversion nanophosphors, J. Am. Chem. Soc., 2011, 133, 15810–15813.

    Article  CAS  PubMed  Google Scholar 

  33. E. Busseron, J. Lux, M. Degardin, J. Rebek Jr., Synthesis and recognition studies with a ditopic, photoswitchable deep cavitand, Chem. Commun., 2013, 49, 4842–4844.

    Article  CAS  Google Scholar 

  34. D. C. Barman, P. Saikia, D. Prajapati, J. S. Sandhu, Heterogeneous permanganate oxidations. a novel method for the deamination using solid supported iron-permanganate, Synth. Commun., 2002, 32, 3407–3412.

    Article  CAS  Google Scholar 

  35. A. Yokoyama, T. Maruyama, K. Tagami, H. Masu, K. Katagiri, I. Azumaya, T. Yokozawa, One-pot synthesis of cyclic triamides with a triangular cavity from trans-stilbene and diphenylacetylene monomers, Org. Lett., 2008, 10, 3207–3210.

    Article  CAS  PubMed  Google Scholar 

  36. M. H. Habibi, A. Hassanzadeh, A. Z. Isfahani, Spectroscopic studies of solophenyl red 3BL polyazo dye tautomerism in different solvents using UV-visible,1H NMR and steady-state fluorescence techniques, Dyes Pigm., 2006, 69, 93–101.

    Article  CAS  Google Scholar 

  37. J. Y. Si, K. Yang, M. Y. Jeong, H. C. Ahn, S. J. Jeon, B. R. Cho, Bis-1,4-(p-diarylaminostryl)-2,5- dicyanobenzene derivatives with large two-photon absorption cross-sections, Org. Lett., 2003, 5, 645–648.

    Article  CAS  Google Scholar 

  38. J. Zhang, J. K. Whitesell, M. A. Fox, Photoreactivity of self-assembled monolayers of azobenzene or stilbene derivatives capped on colloidal gold clusters, Chem. Mater., 2001, 13, 2323–2331.

    Article  CAS  Google Scholar 

  39. M. Elbing, A. Blaszczyk, C. V. Hanisch, M. Mayor, V. Ferri, C. Grave, M. A. Rampi, G. Pace, P. Samori, A. Shaporenko, M. Zharnikov, Single component self-assembled monolayers of aromatic azo-biphenyl: influence of the packing tightness on the SAM structure and light-induced molecular movements, Adv. Funct. Mater., 2008, 18, 2972–2983.

    Article  CAS  Google Scholar 

  40. N. Liu, Z. Chen, D. R. Dunphy, Y. B. Jiang, R. A. Assink, C. J. Brinker, Photoresponsive nanocomposite formed by self-assembly of an azobenzene-modified silane, Angew. Chem. Int. Ed., 2003, 42, 1731–1734.

    Article  CAS  Google Scholar 

  41. Z. Y. Yang, Z. G. Chi, T. Yu, X. Q. Zhang, M. N. Chen, B. J. Xu, S. W. Liu, Y. Zhang, J. R. Xu, Triphenylethylene carbazole derivatives as a new class of AIE materials with strong blue light emission and high glass transition temperature, J. Mater. Chem., 2009, 19, 5541–5546.

    Article  CAS  Google Scholar 

  42. V. Bhalla, S. Kaur, V. Vij, M. Kumar, Mercury-modulated supramolecular assembly of a hexaphenylbenzene derivative for selective detection of picric acid, Inorg. Chem., 2013, 52, 4860–4865.

    Article  CAS  PubMed  Google Scholar 

  43. S. Dong, Z. Li, J. Qin, New carbazole-based fluorophores: synthesis, characterization, and aggregation-induced emission enhancement, J. Phys. Chem. B, 2009, 113, 434–441.

    Article  CAS  PubMed  Google Scholar 

  44. Z. Wang, A. M. Nygard, M. J. Cook, D. A. Russell, An evanescent-field-driven self-assembled molecular photoswitch for macrocycle coordination and release, Langmuir, 2004, 20, 5850–5857.

    Article  CAS  PubMed  Google Scholar 

  45. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. A. Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford, CT, 2004.

    Google Scholar 

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Correspondence to Ayyanar Siva.

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Electronic supplementary information (ESI) available. See DOI: 10.1039/c5pp00357a

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Sivamani, J., Balasaravanan, R., Duraimurugan, K. et al. Synthesis, characterization and photophysical studies of self-assembled azo biphenyl urea derivatives. Photochem Photobiol Sci 15, 211–218 (2016). https://doi.org/10.1039/c5pp00357a

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