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Recently, creating unnatural fluorescent nucleobase analogues has gained increasing attention. In this work, a detailed computational investigation on the photophysical properties of the fluorescent adenine analogue x-adenine (xA) is carried out. The ten lowest low-lying exited states are analyzed and assigned. The effects of methanol solution, linking to deoxyribose, and base pairing on its absorption and emission processes are considered. The calculated excitation and emission energies are in good agreement with the measured data available. It is found that linking to deoxyribose and methanol solution have a hyperchromic effect on xA. Also it is found that methanol solution and linking to deoxyribose will lead to the red shift of fluorescence, while base pairing does not have obvious effects on the lowest ππ* state and fluorescence emission but produces the blue shift of lowest nπ* to some extent.
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Keywords:
- x-adenine /
- electronic spectra /
- fluorescence spectra /
- time-dependent density functional theory
[1] Cobb A J A 2007 Org. Biomol. Chem. 5 3260
[2] Petersen M, Wengel J 2003 Trends Biotechnol. 21 74
[3] Kool E T 2002 Acc. Chem. Res. 35 936
[4] Hirao I 2006 Curr. Opin. Chem. Biol. 10 622
[5] Liu H, Gao J, Lynch S R, Saito Y D, Maynard L, Kool E T 2003 Science 302 868
[6] Gao J, Liu H, Kool E T 2004 J. Am. Chem. Soc. 126 11826
[7] Liu H, Gao J, Kool E T 2005 J. Am. Chem. Soc. 127 1396
[8] Liu H, Gao J, Kool E T 2005 J. Org. Chem. 70 639
[9] Krueger A T, Kool E T 2008 J. Am. Chem. Soc. 130 3989
[10] Fuentes-Cabrera M, Zhao X, Kent P R C, Sumpter B G 2006 J. Phys. Chem. B 110 6379
[11] Runge E, Gross E K U 1984 Phys. Rev. Lett. 52 997
[12] Wang F, Zhang F, Eric S 2003 Chin. Phys. 12 164
[13] Qiu Y, Zhang Y, Wang S 2004 Acta Chim. Sin. 20 2030
[14] Frisch M J, Trucks G W, Schlegel H B et al. 2003 Gaussian 03, Revision B. 03, Gaussian, Inc, Pittsburgh, P A
[15] Becke A D 1993 J. Chem. Phys. 98 5648
[16] Lee C, Yang W, Parr R G 1988 Phys. Rev. B: Condens. Matter 37 785
[17] Foresman J B, Head-Gordon M, Pople J A, Frisch M J 1992 J. Phys. Chem. 96 135
[18] Miertus S, Scrocco E, Tomasi J 1981 Chem. Phys. 55 117
[19] Miertus S, Tomasi J 1982 Chem. Phys. 65 239
[20] Gorelsky S I 2008 SWizard Program, CCRI, University Of Ottawa: Ottawa, Canada, 2008 http: //www.sg-chem.net/
[21] Clark A E, Qin C, Li A D Q 2007 J. Am. Chem. Soc. 129 7586
[22] Dreuw A, Head-Gordon M 2005 Chem. Rev. 105 4009
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[1] Cobb A J A 2007 Org. Biomol. Chem. 5 3260
[2] Petersen M, Wengel J 2003 Trends Biotechnol. 21 74
[3] Kool E T 2002 Acc. Chem. Res. 35 936
[4] Hirao I 2006 Curr. Opin. Chem. Biol. 10 622
[5] Liu H, Gao J, Lynch S R, Saito Y D, Maynard L, Kool E T 2003 Science 302 868
[6] Gao J, Liu H, Kool E T 2004 J. Am. Chem. Soc. 126 11826
[7] Liu H, Gao J, Kool E T 2005 J. Am. Chem. Soc. 127 1396
[8] Liu H, Gao J, Kool E T 2005 J. Org. Chem. 70 639
[9] Krueger A T, Kool E T 2008 J. Am. Chem. Soc. 130 3989
[10] Fuentes-Cabrera M, Zhao X, Kent P R C, Sumpter B G 2006 J. Phys. Chem. B 110 6379
[11] Runge E, Gross E K U 1984 Phys. Rev. Lett. 52 997
[12] Wang F, Zhang F, Eric S 2003 Chin. Phys. 12 164
[13] Qiu Y, Zhang Y, Wang S 2004 Acta Chim. Sin. 20 2030
[14] Frisch M J, Trucks G W, Schlegel H B et al. 2003 Gaussian 03, Revision B. 03, Gaussian, Inc, Pittsburgh, P A
[15] Becke A D 1993 J. Chem. Phys. 98 5648
[16] Lee C, Yang W, Parr R G 1988 Phys. Rev. B: Condens. Matter 37 785
[17] Foresman J B, Head-Gordon M, Pople J A, Frisch M J 1992 J. Phys. Chem. 96 135
[18] Miertus S, Scrocco E, Tomasi J 1981 Chem. Phys. 55 117
[19] Miertus S, Tomasi J 1982 Chem. Phys. 65 239
[20] Gorelsky S I 2008 SWizard Program, CCRI, University Of Ottawa: Ottawa, Canada, 2008 http: //www.sg-chem.net/
[21] Clark A E, Qin C, Li A D Q 2007 J. Am. Chem. Soc. 129 7586
[22] Dreuw A, Head-Gordon M 2005 Chem. Rev. 105 4009
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