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A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on the Distyryl−Bodipy Fluorophore

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Department of Chemistry, Middle East Technical University, Ankara, Turkey TR-06531, Department of Chemistry, Suleyman Demirel University, Isparta, Turkey TR-32260, and Department of Chemistry and UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara, Turkey, TR-06800
†Middle East Technical University.
‡Suleyman Demirel University.
§Bilkent University.
Cite this: Org. Lett. 2008, 10, 18, 4065–4067
Publication Date (Web):August 15, 2008
https://doi.org/10.1021/ol801554t
Copyright © 2008 American Chemical Society

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    77. Ana B. Descalzo, Pichandi Ashokkumar, Zhen Shen, Knut Rurack. On the Aggregation Behaviour and Spectroscopic Properties of Alkylated and Annelated Boron‐Dipyrromethene (BODIPY) Dyes in Aqueous Solution. ChemPhotoChem 2020, 4 (2) , 120-131. https://doi.org/10.1002/cptc.201900235
    78. Li Yan, Xiaoye Wen, Zhefeng Fan. A large-Stokes-shift fluorescent probe for Zn2+ based on AIE, and application in live cell imaging. Analytical and Bioanalytical Chemistry 2020, 412 (6) , 1453-1463. https://doi.org/10.1007/s00216-019-02378-w
    79. Katherine L. VanDenburgh, Yun Liu, Tumpa Sadhukhan, Christopher R. Benson, Natalie M. Cox, Sundus Erbas-Cakmak, Bo Qiao, Xinfeng Gao, Maren Pink, Krishnan Raghavachari, Amar H. Flood. Multi-state amine sensing by electron transfers in a BODIPY probe. Organic & Biomolecular Chemistry 2020, 18 (3) , 431-440. https://doi.org/10.1039/C9OB02466B
    80. Mathappan Mariyappan, Nelson Malini, Jayaraman Sivamani, Gandhi Sivaraman, Muniyasamy Harikrishnan, Sepperumal Murugesan, Ayyanar Siva. Turn-on Fluorescence Chemosensor for Zn2+ Ion Using Salicylate Based Azo Derivatives and their Application in Cell-Bioimaging. Journal of Fluorescence 2019, 29 (3) , 737-749. https://doi.org/10.1007/s10895-019-02382-4
    81. Xujun Zheng, Wencheng Zhu, Fan Ni, Hua Ai, Shaolong Gong, Xiang Zhou, Jonathan L. Sessler, Chuluo Yang. Simultaneous dual-colour tracking lipid droplets and lysosomes dynamics using a fluorescent probe. Chemical Science 2019, 10 (8) , 2342-2348. https://doi.org/10.1039/C8SC04462G
    82. Sabyasachi Ta, Sudipta Das, Milan Ghosh, Mahuya Banerjee, Sumit Kumar Hira, Partha Pratim Manna, Debasis Das. A unique benzimidazole-naphthalene hybrid molecule for independent detection of Zn2+ and N3− ions: Experimental and theoretical investigations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2019, 209 , 170-185. https://doi.org/10.1016/j.saa.2018.10.006
    83. Amy M. Bittel, Ashley M. Davis, Lei Wang, Michel A. Nederlof, Jorge O. Escobedo, Robert M. Strongin, Summer L. Gibbs. Varied Length Stokes Shift BODIPY-Based Fluorophores for Multicolor Microscopy. Scientific Reports 2018, 8 (1) https://doi.org/10.1038/s41598-018-22892-8
    84. Fumitoshi Yagishita, Chiho Nii, Yoshihiko Tezuka, Atsushi Tabata, Hideaki Nagamune, Naohiro Uemura, Yasushi Yoshida, Takashi Mino, Masami Sakamoto, Yasuhiko Kawamura. Fluorescent N‐Heteroarenes Having Large Stokes Shift and Water Solubility Suitable for Bioimaging. Asian Journal of Organic Chemistry 2018, 7 (8) , 1614-1619. https://doi.org/10.1002/ajoc.201800250
    85. Manoj M. Jadhav, Dinesh Patil, Nagaiyan Sekar. Highly Stoke shifted near infrared (NIR) emitting donor-pi-acceptor chromophore: Synthesis and combined experimental and computational studies of photophysical properties. Journal of Photochemistry and Photobiology A: Chemistry 2018, 363 , 13-22. https://doi.org/10.1016/j.jphotochem.2018.05.028
    86. Kanokthorn Boonkitpatarakul, Atchareeporn Smata, Kantapong Kongnukool, Suphongphan Srisurichan, Kittipong Chainok, Mongkol Sukwattanasinitt. An 8-aminoquinoline derivative as a molecular platform for fluorescent sensors for Zn(II) and Cd(II) ions. Journal of Luminescence 2018, 198 , 59-67. https://doi.org/10.1016/j.jlumin.2018.01.048
    87. Huihui Zhang, Zeyue Wei, Ying Xia, Min Fang, Weiju Zhu, Xingyuan Yang, Fei Li, Yupeng Tian, Xuanjun Zhang, Hongping Zhou. Exploration research on synthesis and application of a new dye containing di-2-picolyamine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2018, 196 , 256-261. https://doi.org/10.1016/j.saa.2018.02.023
    88. Shuai Xia, Jinjin Shen, Jianbo Wang, Hailong Wang, Mingxi Fang, Hongwei Zhou, Marina Tanasova. Ratiometric fluorescent and colorimetric BODIPY-based sensor for zinc ions in solution and living cells. Sensors and Actuators B: Chemical 2018, 258 , 1279-1286. https://doi.org/10.1016/j.snb.2017.11.129
    89. Miao Li, Jiangli Fan, Jianjun Du, Jianfang Cao, Xiaojun Peng. Inhibiting proton interference in PET chemosensors by tuning the HOMO energy of fluorophores. Sensors and Actuators B: Chemical 2018, 259 , 626-632. https://doi.org/10.1016/j.snb.2017.12.117
    90. Fabio Cucinotta, Benjamin P. Jarman, Calvin Caplan, Sharon J. Cooper, Helen J. Riggs, Jonathan Martinelli, Kristina Djanashvili, Emanuele La Mazza, Fausto Puntoriero. Light‐Harvesting Antennae using the Host–Guest Chemistry of Mesoporous Organosilica. ChemPhotoChem 2018, 2 (3) , 196-206. https://doi.org/10.1002/cptc.201700144
    91. Guangfu Wu, Qi Gao, Mingxin Li, Xin Tang, King Wai Chiu Lai, Qingxiao Tong. A ratiometric probe based on coumarin-quinoline for highly selective and sensitive detection of Zn2+ ions in living cells. Journal of Photochemistry and Photobiology A: Chemistry 2018, 355 , 487-495. https://doi.org/10.1016/j.jphotochem.2017.05.006
    92. Zheng-Yi Li, Hong-Kui Su, Kun Zhou, Bao-Zhu Yang, Tangxin Xiao, Xiao-Qiang Sun, Juli Jiang, Leyong Wang. Oxo-spirocyclic structure bridged ditopic Schiff base: A turn-on fluorescent probe for selective recognition of Zn(II) and its application in biosensing. Dyes and Pigments 2018, 149 , 921-926. https://doi.org/10.1016/j.dyepig.2017.12.002
    93. Jik Chin, Hae-Jo Kim. Near-infrared fluorescent probes for peptidases. Coordination Chemistry Reviews 2018, 354 , 169-181. https://doi.org/10.1016/j.ccr.2017.07.009
    94. Serkan Erdemir, Begum Tabakci. Selective and Sensitive Fluorescein-Benzothiazole Based Fluorescent Sensor for Zn2+ Ion in Aqueous Media. Journal of Fluorescence 2017, 27 (6) , 2145-2152. https://doi.org/10.1007/s10895-017-2153-8
    95. Simin Belali, Ganapathi Emandi, Atillio A. Cafolla, Barry O’Connell, Benjamin Haffner, Matthias E. Möbius, Alireza Karimi, Mathias O. Senge. Water-soluble, neutral 3,5-diformyl-BODIPY with extended fluorescence lifetime in a self-healable chitosan hydrogel. Photochemical & Photobiological Sciences 2017, 16 (11) , 1700-1708. https://doi.org/10.1039/c7pp00316a
    96. Pramod Kumar Mehta, Eun-Taex Oh, Heon Joo Park, Keun-Hyeung Lee. Ratiometric fluorescent probe based on symmetric peptidyl receptor with picomolar affinity for Zn2+ in aqueous solution. Sensors and Actuators B: Chemical 2017, 245 , 996-1003. https://doi.org/10.1016/j.snb.2017.01.154
    97. Palakuri Ramesh, Jeny Karabline-Kuks, Mor Weiss-Shtofman, Moshe Portnoy. Design and Synthesis of BODIPY-Cored Near IR-emitting Lipophilic and Water-Soluble Dendritic Platforms. ChemistrySelect 2017, 2 (10) , 3093-3098. https://doi.org/10.1002/slct.201700377
    98. Denis Frath, Pascal Didier, Yves Mély, Julien Massue, Gilles Ulrich. Vectorization and Intracellular Distribution of a Two‐Photon‐Absorbing, Near‐Infrared‐Emitting π‐Extended Boranil Dye. ChemPhotoChem 2017, 1 (4) , 109-112. https://doi.org/10.1002/cptc.201700012
    99. Lingyun Wang, Lanqing Li, Derong Cao. Synthesis, photoluminescence, chromogenic and fluorogenic discrimination of fluoride and cyanide based on a triphenylamine-tri(2-formyl BODIPY) conjugate. Sensors and Actuators B: Chemical 2017, 241 , 1224-1234. https://doi.org/10.1016/j.snb.2016.10.007
    100. Mukesh Kumar, Amit Kumar, Mantu Kumar Singh, Sumanta K. Sahu, Rohith P. John. A novel benzidine based Schiff base “turn-on” fluorescent chemosensor for selective recognition of Zn2+. Sensors and Actuators B: Chemical 2017, 241 , 1218-1223. https://doi.org/10.1016/j.snb.2016.10.008
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