“Push–pull” 1,8-naphthalic anhydride with multiple triphenylamine groups as electron donor

作者: Limin Wang , Yan Shi , Yingyuan Zhao , Heyuan Liu , Xiyou Li

DOI: 10.1016/J.MOLSTRUC.2013.10.004

关键词:

摘要: Abstract In this paper, the “push–pull” molecules consisting of different number triphenylamino groups and 1,8-naphthalic anhydride ring were designed synthesized. The UV–vis absorption emission spectra these compounds recorded. Along with increase on electron donating groups, both bands show significant red shift. More importantly, fluorescence quantum yields drop sharply along groups. molecular structure, frontier orbital energies energy gaps between highest occupied (HOMO) lowest un-occupied (LUMO) calculated DFT method. results indicate that connection more in molecule caused a change for first excited state from an intramolecular charge transfer (ICT) to (ET). This has led quenching.

参考文章(27)
Emma B. Veale, Daniel O. Frimannsson, Mark Lawler, Thorfinnur Gunnlaugsson, 4-Amino-1,8-naphthalimide-based Tröger's bases as high affinity DNA targeting fluorescent supramolecular scaffolds Organic Letters. ,vol. 11, pp. 4040- 4043 ,(2009) , 10.1021/OL9013602
Zhi Cao, Premchendar Nandhikonda, Michael D. Heagy, Highly water-soluble monoboronic acid probes that show optical sensitivity to glucose based on 4-sulfo-1,8-naphthalic anhydride. Journal of Organic Chemistry. ,vol. 74, pp. 3544- 3546 ,(2009) , 10.1021/JO9002008
A.Yu Kobitski, R Scholz, D.R.T Zahn, Theoretical studies of the vibrational properties of the 3,4,9,10,-perylene tetracarboxylic dianhydride (PTCDA) molecule Journal of Molecular Structure-theochem. ,vol. 625, pp. 39- 46 ,(2003) , 10.1016/S0166-1280(02)00755-8
Ivo Grabchev, Jean-Marc Chovelon, Photodegradation of poly(amidoamine) dendrimers peripherally modified with 1,8-naphthalimide units Polymer Degradation and Stability. ,vol. 92, pp. 1911- 1915 ,(2007) , 10.1016/J.POLYMDEGRADSTAB.2007.06.018
Alan E. Reed, Larry A. Curtiss, Frank Weinhold, Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Chemical Reviews. ,vol. 88, pp. 899- 926 ,(1988) , 10.1021/CR00088A005
Wei Jiang, Yueming Sun, Xiaoliang Wang, Qi Wang, Wenlian Xu, Synthesis and photochemical properties of novel 4-diarylamine-1,8-naphthalimide derivatives Dyes and Pigments. ,vol. 77, pp. 125- 128 ,(2008) , 10.1016/J.DYEPIG.2007.03.017
Amelia A. Fuller, Frederick J. Seidl, Paul A. Bruno, Marisa A. Plescia, Kanwal S. Palla, Use of the environmentally sensitive fluorophore 4‐N,N‐dimethylamino‐1,8‐naphthalimide to study peptoid helix structures Biopolymers. ,vol. 96, pp. 627- 638 ,(2011) , 10.1002/BIP.21605
David F. Cauble, Vincent Lynch, Michael J. Krische, Studies on the Enantioselective Catalysis of Photochemically Promoted Transformations: “Sensitizing Receptors” as Chiral Catalysts Journal of Organic Chemistry. ,vol. 68, pp. 15- 21 ,(2003) , 10.1021/JO020630E
Kate K Ong, James O Jensen, Hendrik F Hameka, Theoretical studies of the infrared and Raman spectra of perylene Journal of Molecular Structure: THEOCHEM. ,vol. 459, pp. 131- 144 ,(1999) , 10.1016/S0166-1280(98)00266-8
Francis D'Souza, Suresh Gadde, D.-M. Shafiqul Islam, Channa A. Wijesinghe, Amy L. Schumacher, Melvin E. Zandler, Yasuyaki Araki, Osamu Ito, Multi-Triphenylamine-Substituted Porphyrin-Fullerene Conjugates as Charge Stabilizing “Antenna−Reaction Center” Mimics The Journal of Physical Chemistry A. ,vol. 111, pp. 8552- 8560 ,(2007) , 10.1021/JP073121V