Emission pathway switching by solvent polarity: Facile synthesis of benzofuran-bipyridine derivatives and turn-on fluorescence probe for zinc ions
作者： Jiyoung Jung , Adriana Dinescu
DOI: 10.1016/J.TETLET.2016.12.039
关键词: Chemistry 、 Solvent 、 Bipyridine 、 Organic chemistry 、 Polarity (physics) 、 Turn (biochemistry) 、 Benzofuran 、 Alkyne 、 Fluorescence 、 Protonation 、 Photochemistry
摘要: Bipyridine attached benzofuran derivatives were prepared by the cyclization of alkyne ortho-substituted phenols. Electronically different substituents, N,N-dibutylamino vs tert-butyl group, on rings. Depending polarity and pH solvent environment, N,N-dialkylamino group participates in two distinctively roles emissive properties, i.e., ICT-type PET-type behaviors. Upon capturing lone-pair electrons groups protonation, ratiometric blue-shift complete turn-on behaviors observed THF MeCN solution, respectively. Such peculiar behavior was further utilized to show sensing zinc ions.
elsevier.com
sci-hub.se 参考文章(52)
Arun A. Tanpure, Seergazhi G. Srivatsan, Conformation-sensitive nucleoside analogues as topology-specific fluorescence turn-on probes for DNA and RNA G-quadruplexes Nucleic Acids Research. ,vol. 43, ,(2015) , 10.1093/NAR/GKV743
Yuncong Chen, Yang Bai, Zhong Han, Weijiang He, Zijian Guo, Photoluminescence imaging of Zn2+ in living systems Chemical Society Reviews. ,vol. 44, pp. 4517- 4546 ,(2015) , 10.1039/C5CS00005J
Haixia Wang, Haixia Wu, Lin Xue, Yan Shi, Xiyou Li, A naphthalimide fluorophore with efficient intramolecular PET and ICT Processes: Application in molecular logic Organic and Biomolecular Chemistry. ,vol. 9, pp. 5436- 5444 ,(2011) , 10.1039/C1OB05481C
Michael Maus, Knut Rurack, Monitoring pH and solvent proticity with donor–acceptor-substituted biphenyls: a new approach towards highly sensitive and powerful fluorescent probes by tuning the molecular structure New Journal of Chemistry. ,vol. 24, pp. 677- 686 ,(2000) , 10.1039/B003819I
Chengliang Li, Yicheng Zhang, Pinhua Li, Lei Wang, Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols. Journal of Organic Chemistry. ,vol. 76, pp. 4692- 4696 ,(2011) , 10.1021/JO200317F
Satoko Maruyama, Kazuya Kikuchi, Tomoya Hirano, Yasuteru Urano, Tetsuo Nagano, A novel, cell-permeable, fluorescent probe for ratiometric imaging of zinc ion. Journal of the American Chemical Society. ,vol. 124, pp. 10650- 10651 ,(2002) , 10.1021/JA026442N
Sushobhan Ghosh, Oscar Mendoza, Leticia Cubo, Frédéric Rosu, Valérie Gabelica, Andrew J. P. White, Ramon Vilar, Assembly of palladium(II) and platinum(II) metallo-rectangles with a guanosine-substituted terpyridine and study of their interactions with quadruplex DNA. Chemistry: A European Journal. ,vol. 20, pp. 4772- 4779 ,(2014) , 10.1002/CHEM.201304905
Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani, Copper catalysis in the construction of indole and benzo[b]furan rings. Organic and Biomolecular Chemistry. ,vol. 9, pp. 641- 652 ,(2011) , 10.1039/C0OB00501K
Ozlem Oter, Kadriye Ertekin, Cumhur Kirilmis, Murat Koca, Misir Ahmedzade, Characterization of a newly synthesized fluorescent benzofuran derivative and usage as a selective fiber optic sensor for Fe(III) Sensors and Actuators B-chemical. ,vol. 122, pp. 450- 456 ,(2007) , 10.1016/J.SNB.2006.06.010
Gilson Zeni, Richard C. Larock, Synthesis of heterocycles via palladium-catalyzed oxidative addition. Chemical Reviews. ,vol. 106, pp. 4644- 4680 ,(2006) , 10.1021/CR0683966