Abstract
Rosette nanotubes (RNTs) are tubular architectures generated through the hierarchical self-assembly of the guanine-cytosine (G∧C) motif1 or2 (Figure 1). Motif2 differs from1 by the substitution at the N-atom in the G-ring with a C-atom as shown in red. In this paper, we prepare a new tricyclic G∧C base3 from a functionalized derivative of2 and demonstrate its self-assembly into fluorescent helical RNTs inN, N-dimethylformamide (DMF). The self-assembly and fluorescent properties of RNTs3 were established using scanning electron microscopy (SEM), transmission electron microscopy (TEM), atomic force microscopy (AFM) and UV-visible spectroscopy.
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G. Chen, Pharmaceut Anal Acta 3: e136. doi:10.4172/2153–2435.1000e136.
Z. Liu, J. T. Robinson, S. M. Tabakmanb, K. Yanga, and H. Dai, Mater. Today 14, 316 (2011).
N. M. Iverson, P. W. Barone, M. Shandell, L. J. Trudel, S. Sen, F. Sen, V. Ivanov, E. Atolia, E. Farias, T. P. McNicholas, N. Reuel, N. M. A. Parry, G. N. Wogan and M. S. Strano, Nat. Nanotechnol 8, 873 (2013).
S. Vardharajula, S. Z Ali, P. M Tiwari, E. Eroglu, K. Vig, V. A Dennis, S. R Singh, Int. J. Nanomedicine 7, 5361 (2012).
A. A. Hariri, G. D. Hamblin, Y. Gidi, H. F. Sleiman and G. Cosa, Nature Chem. 7, 295 (2015).
Y. Zhou, M. Kogiso, C. He, Y. Shimizu, N. Koshizaki, and T. Shimizu, Adv. Mater. 19, 1055 (2007).
J. Montenegro, C. Vázquez-Vázquez, A. Kalinin, K. E. Geckeler and J. R. Granja, J. Am. Chem. Soc. 136, 2484 (2014).
R. L. Beingessner, B.-L. Deng, P. E. Fanwick and H. Fenniri, J. Org. Chem. 73, 931 (2008).
G. Borzsonyi, R. L. Beingessner, T. Yamazaki, J. Y. Cho, A. J. Myles, M. Malac, R. Egerton, M. Kawasaki, K. Ishizuka, A. Kovalenko and H. Fenniri, J. Am. Chem. Soc. 132, 15136(2010).
G. Borzsonyi, R. S. Johnson, A. J. Myles, J.-Y. Cho, T. Yamazaki, R. L. Beingessner, A. Kovalenko and H. Fenniri, Chem. Commun. 46, 6527 (2010).
G. Borzsonyi, A. Alsbaiee, R. L. Beingessner and H. Fenniri, J. Org. Chem. 75, 7233 (2010).
R. Chhabra, J. G. Moralez, J. Raez, T. Yamazaki, J.-Y. Cho, A. J. Myles, A. Kovalenko and H. Fenniri, J. Am. Chem. Soc. 132, 32 (2009).
G. Tikhomirov, M. Oderinde, D. Makeiff, A. Mansouri, W. Lu, F. Heirtzler, S. Kingsley, D. Y. Kwok and H. Fenniri, J. Org. Chem. 73, 4248 (2008).
B.-L. Deng, R. L. Beingessner, R. S. Johnson, N. K Girdhar, C. Danumag, T. Yamazaki, and H. Fenniri, Macromolecules 45, 7157 (2012).
A. Alsbaiee, M. St. Jules, R. L. Beingessner, T. Yamazaki, J. Y. Cho and H. Fenniri, Tet. Lett. 53, 1645 (2012).
U. D. Hemraz, M. El-Bakkari, T. Yamazaki, J.-Y. Cho, R. L. Beingessner and H. Fenniri, Nanoscale 6, 9421 (2014).
R. L. Beingessner, J. A. Diaz, U. D. Hemraz and H. Fenniri, Tet. Lett. 52, 661 (2011).
J. Raez, J. G. Moralez and H. Fenniri, J. Am. Chem. Soc. 126, 16298 (2004).
T. Yamazaki, H. Fenniri and A. Kovalenko, ChemPhysChem 11, 361 (2010).
R. S. Johnson, T. Yamazaki, A. Kovalenko and H. Fenniri, J. Am. Chem. Soc. 129, 5735 (2007).
L. Shuai, V. Parthasarathy, J.-Y. Cho, T. Yamazaki, D. A. Makeiff, R. L. Beingessner and H. Fenniri, Mater. Res. Soc. Symp. Proc. 1737, mrsf14-1737-u01-04 (2015).
A. Alsbaiee, M. El-Bakkari and H. Fenniri, Mater. Res. Soc. Symp. Proc. 1316, mrsf10-1316-qq 12–18 (2011).
M. El-Bakkari, R. L. Beingessner, A. Alshamsan, J.-Y. Cho and H. Fenniri, Mater. Res. Soc. Symp. Proc. 1316, mrsf10-1316-qq 12–16 (2011).
A. Alshamsan, M. El-Bakkari and H. Fenniri, Mater. Res. Soc. Symp. Proc. 1316, mrsf10-1316-qq 09–36 (2011).
U. D. Hemraz and H. Fenniri, Mater. Res. Soc. Symp. Proc. 1057, 1057-1105-37 (2008).
H. Fenniri, P. J. Mathivanan, K. L. Vidal, D. M. Sherman, K J. Hallenga, K. L. Wood and J. G. Stowell, J. Am. Chem. Soc. 123, 3854 (2001).
H. Fenniri, B.-L. Deng and A. E. Ribbe, J. Am. Chem. Soc. 124, 11064 (2002).
H. Fenniri, B.-L. Deng, A. E. Ribbe, K Hallenga, J. Jacob and P. Thiyagarajan, Proc. Natl. Acad Sci. U.SA. 99, 6487 (2002).
L. Zhang, F. Rakotondradany, A. J. Myles and H. Fenniri, Biomaterials 30, 1309 (2009).
X. Meng, D. A. Stout, L. Sun, R. L. Beingessner, H. Fenniri and T. J. Webster, J. Biomed Mater Res Part A, 101A, 1095 (2012).
L. Zhang, U. D. Hemraz, H. Fenniri and T. J. Webster, J. Biomed. Mater. Res. 95A, 550 (2010).
A. L. Chun, J. G. Moralez, H. Fenniri and T. J. Webster, Nanotechnology 15, S234 (2004).
L. Zhang, J. Rodriguez, J. Raez, A. J. Myles, H. Fenniri and T. J. Webster, Nanotechnology 20, 175101 (2009).
Y. Chen, S. Song, Z. Yan, H. Fenmn and T. J. Webster, Int. J. Nanomed 6, 1035 (2011).
W. S. Journeay, S. S. Suri, J. G. Moralez, H. Fenniri and B. Singh, Small 5, 1446 (2009).
L. Zhang, S. Ramsaywack, H. Fenniri and T. J. Webster, Tissue Engineering Part A 14, 1353 (2008).
S. S. Singh, S. Mills, G. K. Aulakh, F. Rakotondradany, H. Fenniri and B. Singh, Int. J. Nanomed. 6, 3113 (2011).
A. Childs, U. D. Hemraz, N. J. Castro, H. Fenniri and L. G. Zhang, Biomed Mater. 8, 065003 (2013).
M. H. A. Le, S. S. Suri, F. Rakotondradany, H. Fenniri and B. Singh, Vet. Res. 41, 75 (2010).
A. L. Chun, J. G. Moralez, T. J. Webster and H. Fenniri, Biomaterials 26, 7304 (2005).
E. Fine, L. Zhang, H. Fenniri and T. J. Webster, Int. J. Nanomed. 4, 91 (2009).
W. S. Journeay, S. S. Singh, J. G. Moralez, H. Fenniri and B. Singh, Int. J. Nanomed 3, 373 (2008).
A. Durmus, G. Gunbas, S. Farmer, M. Olmstead, M. Mascai, B. Legesse, J.-Y. Cho, R. L. Beingessner, T. Yamazaki and H. Fenniri, J. Org. Chem. 78, 11421 (2013).
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Legesse, B., Cho, JY., Beingessner, R.L. et al. Fluorescent Rosette Nanotubes from the C-analogue of the Guanine–Cytosine (G∧C) Motif. MRS Online Proceedings Library 1796, 1–6 (2015). https://doi.org/10.1557/opl.2015.523
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DOI: https://doi.org/10.1557/opl.2015.523