A novel NIR violanthrone derivative with high electron-deficiency: effect of fluorescence on dicyanomethylene substitution
Tóm tắt
Near infrared (NIR) dyes attracted increasing interests in widely potential applications, such as fluorescent probe and living organism imaging, due to their low background signals from biomolecules, low light scattering and deep penetration, and low-cost excitation light sources. A novel NIR violanthrone derivative (VA-CN) with dicyanomethylene substitution was synthesized and fully characterized by 1H NMR, 13C NMR, HRMS, and IR spectrometry. It is demonstrated that the original planar conformation of violanthrone ring (the nine fused benzene rings) becomes twisted and unsymmetrical upon the incorporation of two strong electron-withdrawing dicyanomethylene units. Photophysical, electrochemical performances as well as distinct solvatochromic effects were studied in detail. Considering the low reduction potential (−0.56 V vs NHE), VA-CN could be considered as a good electron acceptor due to the strong electron deficiency resulted from dicyanomethylene group. A distinct increase in fluorescence was observed with 30-fold enhancement upon the addition of n-butyl amine. The reversible fluorescence “off-on” shows that VA-CN might be served as a promising fluorescent sensor for electron-rich amines.
Tài liệu tham khảo
Umezawa, K.; Nakamura, Y.; Makino, H.; Citterio, D.; Suzuki, K., J. Am. Chem. Soc. 2008, 130, 1550–1551
Weissleder, R., Nat. Biotechnol. 2001, 19, 316–317
Tang, B.; Cui, L. J.; Xu, K. H.; Tong, L. L.; Yang, G. W.; An, L. G., ChemBioChem 2008, 9, 1159–1164
Meguellati, K.; Spichty, M.; Ladame, S., Org. Lett. 2009, 11, 1123–1126
Lee, H.; Mason, J. C.; Achilefu, S., J. Org. Chem. 2008, 73, 723–725
Geiger, T.; Kuster, S.; Yum, J. H.; Moon, S. J.; Nazeeruddin, M. K.; Grätzel, M.; Nüesch, F., Adv. Funct. Mater. 2009, 19, 2720–2727
Dilek, G.; Akkaya, E. U., Tetrahedron Lett. 2000, 41, 3721–3724
Yagi, S.; Ohta, T.; Akagi, N.; Nakazumi, H., Dyes Pigments 2008, 77, 525–536
Bae, J. S.; Gwon, S. Y.; Son, Y. A.; Kim, S. H., Dyes Pigments 2009, 83, 324–327
Loudet, A.; Burgess, K., Chem. Rev. 2007, 107, 4891–4932
Wang, Y. W.; Yu, M. X.; Yu, Y. H.; Bai, Z. P.; Shen, Z.; Li, F. Y.; You, X. Z., Tetrahedron Lett. 2009, 50, 6169–6172
Tian, M.; Peng, X.; Feng, F.; Meng, S.; Fan, J.; Sun, S., Dyes Pigments 2009, 81, 58–62
Hansongnern, K.; Chooto, P.; Amornpitoksuk, P., Int. J. Photoenergy 1999, 1, 143–145
Inokuchi, H., Org. Electron. 2006, 7, 62–76
Cabanillas-Gonzalez, J.; Yeates, S.; Bradley, D. D. C., Synth. Met. 2003, 139, 637–641
Seybold, G.; Wagenblast, G., Dyes Pigments 1989, 11, 303–317
Rauhut, M. M.; Roberts, B. G.; Maulding, D. R.; Bergmark, W.; Coleman, R., J. Org. Chem. 1975, 40, 330–335
Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; et al., Gaussian 03, revision C.01, Gaussian, Inc.: Pittsburgh, PA, 2004
Becke, A. D., J. Chem. Phys. 1993, 98, 5648–5652
Ditchfield, R.; Herhe, W. J.; Pople, J. A., J. Chem. Phys. 1971, 54, 724–728
Isborn, C. M.; Leclercq, A.; Vila, F. D.; Dalton, L. R.; Brédas, J. L.; Eichinger, B. E.; Robinson, B. H., J. Phys. Chem. A 2007, 111, 1319–1327
Liu, B.; Zhu, W. H.; Zhang, Q.; Wu, W. J.; Xu, M.; Ning, Z. J.; Xie, Y. S.; Tian, H., Chem. Commun. 2009, 1766–1768
Mishra, A.; Fischer, M. K. R.; Bäuerle, P., Angew. Chem. Int. Ed. 2009, 48, 2474–2499
Suzuki, T.; Ichioka, K.; Higuchi, H.; Kawai, H.; Fujiwara, K.; Ohkita, M.; Tsuji, T.; Takahashi, Y., J. Org. Chem. 2005, 70, 5592–5598
Fabian, J.; Nakazumi, H.; Matsuoka, M., Chem. Rev. 1992, 92, 1197–1226
Valeur, R., Molecular Fluorescence: Principles and Applications; Wiley-VCH: Verlag GmbH, 2001, p 200–225
Jacob, J.; Sax, S.; Piok, T.; List, E. J. W.; Grimsdale, A. C.; Müllen, K., J. Am. Chem. Soc. 2004, 126, 6987–6995