Abstract
Photo-reactions of molecules with two [2π + 2π]-cycloaddition sites in the solid state are reported. Four thyminyl stilbazoles having both a stilbazole olefin and a thyminyl olefin were synthesized using the Heck reaction of halo-pyridine substrates with vinylbenzyl thymine or methylated vinylbenzylthymine. Only one of them, methylated vinylbenzylthymine with 4-pyridine, was photoreactive and formed a head-to-tail stilbazole dimer. The crystal structures of thyminyl stilbazoles and the stilbazole dimer were used to investigate the structure—reactivity relationships.
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K. Biradha and R. Santra, Crystal engineering of topochemical solid state reactions, Chem. Soc. Rev., 2013, 42, 950–967.
A. Matsumoto, Reaction of 1,3-diene compounds in the crystalline state, Top. Curr. Chem., 2005, 254, 263–305.
P. Klán and J. Wirz, Chemistry of excited molecules, in Photochemistry of Organic Compounds, John Wiley & Sons, Ltd, 2009, pp. 227–453.
G. Kaur, P. Johnston and K. Saito, Photo-reversible reactions and their applications in polymeric systems, Polym. Chem., 2014, 5, 2171–2186.
A. Sergeiko, V. V. Poroikov, L. O. Hanu and V. M. Dembitsky, Cyclobutane-containing alkaloids: Origin, synthesis, and biological activities, Open Med. Chem. J., 2008, 2, 26–37.
G. M. J. Schmidt, Photodimerizations in the solid state, Pure Appl. Chem., 1971, 27, 647–678.
K. Gnanaguru, N. Ramasubbu, K. Venkatesan and V. Ramamurthy, A study on the photochemical dimerization of coumarins in the solid state, J. Org. Chem., 1985, 50, 2337–2346.
H. Kashida, T. Doi, T. Sakakibara, T. Hayashi and H. Asanuma, p-stilbazole moieties as artifical base pair for photo-cross-linking of DNA duplex, J. Am. Chem. Soc., 2013, 135, 7960–7966.
M. Pattabiraman, A. Natarajan, R. Kaliappan, J. T. Mague and V. Ramamurthy, Template directed photodimerization of trans-1,2-bis(n-pyridyl)ethylenes and stilbazoles in water, Chem. Commun., 2005, 4542–4544.
B. Mondal, B. Captain and V. Ramamurthy, Photodimerization of HCl salts of azastilbenes in the solid state, Photochem. Photobiol. Sci., 2011, 10, 891–894.
D. Bucar, A. Sen, S. V. Santhana Mariappana and L. R. MacGillivray, A [2+2] cross-photodimerisation of photostable olefinsvia a three-component cocrystal solid solution, Chem. Commun., 2012, 48, 1790–1792.
E. Elacqua, R. C. Laird and L. R. MacGillivray, Templated [2+2] photodimerizations in the solid state, in Supramolecular Chemistry: From Molecules to Nanomaterials, ed. P. A. Gale and J. W. Steed, John Wiley & Sons, Ltd, 2012, vol. 6 pp. 3153–3165.
J. Cadet and P. Vigny, The photochemistry of nucleic acids, in Bioorganic Photochemistry, ed. H. Morrison, John Wiley & Sons, Ltd, 1990, vol. 1 pp. 1–272.
P. Johnston, C. Braybrook and K. Saito, Topochemical photo-reversible polymerization of a bioinspired monomer and its recovery and repolymerization after photo-depolymerization, Chem. Sci., 2012, 3, 2301–2306.
P. Johnston, E. I. Izagorodina and K. Saito, The interplay between hydrogen bonding and p-p stacking interactions in the crystal packing of N1-thyminyl derivatives, and implications to the photo-chemical [2π+2π]-cycloaddition of thyminyl compounds, Photochem. Photobiol. Sci., 2012, 11, 1938–1951.
J. Cadet, S. Courdavault, J. L. Ravanat and T. Douki, UVB and UVA radiation-mediated damage to isolated and cellular DNA, Pure Appl. Chem., 2005, 77, 947–961.
R. B. Setlow, Repair deficient human disorder and cancer, Nature, 1978, 271, 713–717.
D. M. Martino, D. Reyna, D. A. Estenoz, S. Trakhtenberg and J. C. Warner, Photosensitization of bioinspired thymine-containing polymers, J. Phys. Chem. A, 2008, 112, 4786–4792.
R. McHale, J. P. Patterson, P. B. Zetterlund, R. K. O’Reilly, Biomimetic radical polymerization via cooperative assembly of segregating templates, Nat. Chem., 2012, 4, 491–497.
J. E. Puskas, Y. Dahman, A. Margaritis and M. Cunningham, Novel thymine-functionalized polystyrenes for applications in biotechnology. 2. adsorption of model proteins, Biomacromolecules, 2004, 5, 1412–1421.
C. M. Cheng, M. I. Egbe, J. M. Grasshoff, D. J. Guarrera, R. P. Pai, J. C. Warner and L. D. Taylor, Synthesis of 1-(vinylbenzyl)thymine, a novel, versatile multi-functional monomer, J. Polym. Sci., Part A: Polym. Chem., 1995, 33, 2515–2519.
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Electronic supplementary information (ESI) available. CCDC 984307, 984308, 984309, 984310, and 984311. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4pp00185k
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Johnston, P., Nishikami, Y. & Saito, K. Synthesis of thyminyl stilbazoles and their photo-reactivity. Photochem Photobiol Sci 13, 1290–1296 (2014). https://doi.org/10.1039/c4pp00185k
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DOI: https://doi.org/10.1039/c4pp00185k