Photophysical Behavior of Heteroduplexes Formed from Naphthalene Incorporated Foldamers, and Linear Donors and Pyromellitic Diimide Incorporated Foldamers

Chemical Research in Chinese Universities ›› 2009, Vol. 25 ›› Issue (3): 317-327.

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Photophysical Behavior of Heteroduplexes Formed from Naphthalene Incorporated Foldamers, and Linear Donors and Pyromellitic Diimide Incorporated Foldamers

ZHAO Shu-min^1,2, GU Hai-ning² and ZHOU Qi-zhong²*

1. Key Laboratory for Molecular Design and Nutrition Engineering of Ningbo, Ningbo Institute of Technology of Zhejiang University, Ningbo 315100, P. R. China;
2. Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China

Received:2008-07-03 Revised:2008-08-25 Online:2009-05-25 Published:2009-08-07
Supported by:
Supported by the Ministry of Science and Technology of China(No.G2000078101) and the National Natural Science Foundation of China(No.20172069).

Abstract

Abstract:

The authors synthesized the electron-rich 1,5-dioxonaphthyl group incorporated foldamers, and linear donors and electron-deficient pyromellitic diimide incorporated foldamers, which were investigated in organic solvents. There is an evident charge transfer process from the donors to the electron-deficient foldamers, due to the donor-acceptor interaction of the heteroduplexes formed from the donors and the electron-deficient foldamers in chloroform, observed by using the ultraviolet(UV) visible method. The charge transfer process of the heteroduplexes depends on the molecular structure(not only the number of 1,5-dioxonaphthyl groups and pyromellitic diimide groups in the heteroduplex, but also the intermolecular double hydrogen bond in the heteroduplex), the intercalative π-π sta- cking motif, the initial concentration of heteroduplexes, and the polarity of the solvent. Fortunately, the authors found a critical bumping concentration(CBC) of the donors in acetonitrile or chloroform, which is useful in quantitative research, by using the fluorescence method. The value of CBC depends not only on intramolecular folding and the intramolecular hydrogen bond, but also on intramolecular π-π stacking and the solvent. The electron-deficient foldamers quenched the fluorescence of the donors. Fluorescence quenching depends not only on the number of pyromellitic diimide groups and 1,5-dioxonaphthyl groups in the heteroduplex, but also on the intercalative π-π stacking motif between the donor and the acceptor.

Key words: Heteroduplex; Foldamer; Linear donor; Charge transfer; Quench

ZHAO Shu-min, GU Hai-ning and ZHOU Qi-zhong*. Photophysical Behavior of Heteroduplexes Formed from Naphthalene Incorporated Foldamers, and Linear Donors and Pyromellitic Diimide Incorporated Foldamers[J]. Chemical Research in Chinese Universities, 2009, 25(3): 317-327.

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Photophysical Behavior of Heteroduplexes Formed from Naphthalene Incorporated Foldamers, and Linear Donors and Pyromellitic Diimide Incorporated Foldamers

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