Temperature‐Dependent Dynamics of Push–Pull Rotor Systems Based on Acridinylidene Cyanoacetic Esters
作者： Marcel Krick , Julian J. Holstein , Axel Wuttke , Ricardo A. Mata , Guido H. Clever
关键词:
摘要: A series of asymmetrically substituted acridinylidene cyanoacetic esters was synthesized and analyzed for dynamic behavior spectroscopic features. Although formally connected via a C=C double bond, the ester groups behave as molecular rotors due to electronic push-pull situation in system. The donor-acceptor character lowers rotational barrier allows controlling rate by adjusting contribution substituent changing solvent polarity. Besides rotation, much faster flipping motion can be assigned tricyclic motif, both which lead rapid interconversion between axially chiral conformers Acid treatment induces an intense fluorescence system, protonation carbon on rotor site, concomitant with formation fluorescent acridinium ion. dynamic, fluorogenic electrochemical three systems is compared aid NMR, UV/vis measurements, X-ray structural analysis, cyclic voltammetry modelling.
sci-hub.se 参考文章(52)
Nagatoshi Koumura, Robert W. J. Zijlstra, Richard A. van Delden, Nobuyuki Harada, Ben L. Feringa, Light-driven monodirectional molecular rotor Nature. ,vol. 401, pp. 152- 155 ,(1999) , 10.1038/43646
Gaku Yamamoto, Megumi Kaneko, Miki Ohkuma, Mao Minoura, Dynamic Stereochemistry of Alkyltris(9-triptycyl)stannanes Chemistry Letters. ,vol. 32, pp. 964- 965 ,(2003) , 10.1246/CL.2003.964
Jeffrey S. Hannam, Stephen M. Lacy, David A. Leigh, Carlos G. Saiz, Alexandra M. Z. Slawin, Sheila G. Stitchell, Controlled submolecular translational motion in synthesis: a mechanically interlocking auxiliary. Angewandte Chemie. ,vol. 43, pp. 3260- 3264 ,(2004) , 10.1002/ANIE.200353606
Florian Weigend, Filipp Furche, Reinhart Ahlrichs, Gaussian basis sets of quadruple zeta valence quality for atoms H–Kr The Journal of Chemical Physics. ,vol. 119, pp. 12753- 12762 ,(2003) , 10.1063/1.1627293
Lijuan Li, Andreas Decken, Brian G. Sayer, Michael J. McGlinchey, Patrick Bregaint, Jean Yves Thepot, Loic Toupet, Jean Rene Hamon, Claude Lapinte, Multiple fluxional processes in chiral (pentaphenylcyclopentadienyl)iron complexes: X-ray crystal structure of (C5Ph5)Fe(CO)(PMe3)(HC:O) and the barriers to aryl, phosphine, and tripodal rotation in (C5Ph5)Fe(CO)(PMe2Ph)C(O)Et Organometallics. ,vol. 13, pp. 682- 689 ,(1994) , 10.1021/OM00014A046
Christoph A. Schalley, Kaweh Beizai, Fritz Vögtle, On the Way to Rotaxane-Based Molecular Motors: Studies in Molecular Mobility and Topological Chirality† Accounts of Chemical Research. ,vol. 34, pp. 465- 476 ,(2001) , 10.1021/AR000179I
Florian Weigend, Reinhart Ahlrichs, Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy Physical Chemistry Chemical Physics. ,vol. 7, pp. 3297- 3305 ,(2005) , 10.1039/B508541A
Aurelio Mateo-Alonso, Christian Ehli, G. M. Aminur Rahman, Dirk M. Guldi, Giulia Fioravanti, Massimo Marcaccio, Francesco Paolucci, Maurizio Prato, Tuning Electron Transfer through Translational Motion in Molecular Shuttles Angewandte Chemie. ,vol. 46, pp. 3521- 3525 ,(2007) , 10.1002/ANIE.200605039
Pi Wang, Yong Yao, Min Xue, A novel fluorescent probe for detecting paraquat and cyanide in water based on pillar[5]arene/10-methylacridinium iodide molecular recognition. Chemical Communications. ,vol. 50, pp. 5064- 5067 ,(2014) , 10.1039/C4CC01403K
Ben L. Feringa, In Control of Motion: From Molecular Switches to Molecular Motors† Accounts of Chemical Research. ,vol. 34, pp. 504- 513 ,(2001) , 10.1021/AR0001721