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Fluorescence Enhancement of Di-p-tolyl Viologen by Complexation in Cucurbit[7]uril

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Chemistry Department, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States
Cite this: J. Am. Chem. Soc. 2012, 134, 7, 3358–3366
Publication Date (Web):February 9, 2012
https://doi.org/10.1021/ja206833z
Copyright © 2012 American Chemical Society

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    Abstract

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    A viologen derivative, 1,1′-di-p-tolyl-(4,4′-bipyridine)-1,1′-diium dichloride (DTV2+), was studied in solution and encapsulated in cucurbit[7]uril (CB7), a macrocyclic host. Upon encapsulation, DTV2+ exhibited dramatically enhanced fluorescence. Aqueous solutions of DTV2+ were weakly fluorescent (Φ = 0.01, τ < 20 ps), whereas the emission of the DTV2+@2CB7 complex was enhanced by 1 order of magnitude (Φ = 0.12, τ = 0.7 ns) and blue-shifted by 35 nm. Similar properties were observed in the presence of NaCl. DTV2+ in a poly(methyl methacrylate) matrix was fluorescent with a spectrum similar to that observed for the complex in solution. 1H NMR and UV–vis titrations indicated that the DTV2+@2CB7 complex is formed in aqueous solutions with complexation constants K1 = (1.2 ± 0.3) × 104 M–1 and K2= (1.0 ± 0.4) × 104 M–1 in water. Density functional theory and configuration interaction singles calculations suggested that the hindrance of the rotational relaxation of the S1 state of DTV2+ caused by encapsulation within the host or a polymer matrix plays a key role in the observed emission enhancement. The absorption and emission spectra of DTV2+@2CB7 in water exhibited a large Stokes shift (ΔSt ∼ 9000 cm–1) and no fine structure. DTV2+ is a good electron acceptor [E°(DTV2+/DTV•+) = −0.30 V vs Ag/AgCl] and a strong photooxidant [E°(DTV*2+/DTV•+) = 0.09 V vs NHE]).

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    Synthesis and characterization of 1, 1H NMR spectra of CB7 and DTV2+, UV–vis spectra for the determination of binding constants, 1H NMR spectra of the CB7 region, absorption and emission spectra of DTV•+, cyclic voltammograms of DTV2+ and DTV2+@2CB7, and experimental procedure for the Job plot. This material is available free of charge via the Internet at http://pubs.acs.org.

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    68. Toshiaki Mori, Yusuke Yoshigoe, Yoichiro Kuninobu. Control of Multicolor and White Emission by Adjusting the Equilibrium between Fluorophores, Lewis Acids, and Their Complexes in Polymers. Angewandte Chemie 2019, 131 (41) , 14599-14603. https://doi.org/10.1002/ange.201903408
    69. Toshiaki Mori, Yusuke Yoshigoe, Yoichiro Kuninobu. Control of Multicolor and White Emission by Adjusting the Equilibrium between Fluorophores, Lewis Acids, and Their Complexes in Polymers. Angewandte Chemie International Edition 2019, 58 (41) , 14457-14461. https://doi.org/10.1002/anie.201903408
    70. Magdalena Olesińska, Guanglu Wu, Silvia Gómez-Coca, Daniel Antón-García, Istvan Szabó, Edina Rosta, Oren A. Scherman. Modular supramolecular dimerization of optically tunable extended aryl viologens. Chemical Science 2019, 10 (38) , 8806-8811. https://doi.org/10.1039/C9SC03057C
    71. Zumei Zhu, Jinqiao Xue, Bin Wen, Weiming Ji, Binyang Du, Jingjing Nie. Ultrasensitive and selective detection of MnO4− in aqueous solution with fluorescent microgels. Sensors and Actuators B: Chemical 2019, 291 , 441-450. https://doi.org/10.1016/j.snb.2019.04.103
    72. Stefan Schoder, Hendrik V. Schröder, Luca Cera, Rakesh Puttreddy, Arne Güttler, Ute Resch‐Genger, Kari Rissanen, Christoph A. Schalley. Strong Emission Enhancement in pH‐Responsive 2:2 Cucurbit[8]uril Complexes. Chemistry – A European Journal 2019, 25 (13) , 3257-3261. https://doi.org/10.1002/chem.201806337
    73. Ting Yin, Sheng Zhang, Mengxuan Li, Carl Redshaw, Xin-Long Ni. Macrocycle encapsulation triggered supramolecular pKa shift: A fluorescence indicator for detecting octreotide in aqueous solution. Sensors and Actuators B: Chemical 2019, 281 , 568-573. https://doi.org/10.1016/j.snb.2018.10.136
    74. Zenghui Han, Qiongbo Zhou, Yaoji Li. Self-assembled (pseudo)rotaxane and polyrotaxane through host–guest chemistry based on the cucurbituril family. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2018, 92 (1-2) , 81-101. https://doi.org/10.1007/s10847-018-0828-7
    75. Sayeed Ashique Ahmed, Soma Seth (Duley), Rajesh Kumar Gautam, Debabrata Seth. Inclusion of a coumarin derivative inside the macrocyclic hosts: A spectroscopic, thermodynamic and theoretical investigation. Journal of Molecular Liquids 2018, 264 , 550-562. https://doi.org/10.1016/j.molliq.2018.05.081
    76. Tae Yong Yun, Hong Chul Moon. Highly stable ion gel-based electrochromic devices: Effects of molecular structure and concentration of electrochromic chromophores. Organic Electronics 2018, 56 , 178-185. https://doi.org/10.1016/j.orgel.2018.02.018
    77. Stephan Sinn, Frank Biedermann. Chemical Sensors Based on Cucurbit[ n ]uril Macrocycles. Israel Journal of Chemistry 2018, 58 (3-4) , 357-412. https://doi.org/10.1002/ijch.201700118
    78. Maali Saad Mokhtar, FakhrEldin O. Suliman, Abdalla A. Elbashir. The binding interaction of imazapyr with cucurbit[ n ]uril (n = 6–8): Combined experimental and molecular modeling study. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2018, 194 , 67-75. https://doi.org/10.1016/j.saa.2018.01.007
    79. Min Jung Lee, Min Kyoung Kim, Nirmal K. Shee, Jooran Lee, Minjoong Yoon, Hee‐Joon Kim. Supramolecular Complexation between Porphyrin‐Viologen Dyad and Cucurbit[7]uril. ChemistrySelect 2018, 3 (1) , 256-261. https://doi.org/10.1002/slct.201702638
    80. Sayeed Ashique Ahmed, Debabrata Seth. Investigation of interaction of an alkaloid harmaline with cucurbit[7]uril: A spectroscopic and calorimetric study. Chemical Physics Letters 2018, 692 , 340-344. https://doi.org/10.1016/j.cplett.2017.12.056
    81. Lubna R. Alrawashdeh, Michael P. Cronin, Anthony I. Day, Lynne Wallace, Clifford E. Woodward. Modelling the luminescence of iridium cyclometalated complexes encapsulated in cucurbituril. The Analyst 2018, 143 (2) , 519-527. https://doi.org/10.1039/C7AN01632H
    82. Ekaterina A. Kovalenko, Ekaterina A. Pashkina, Lyubov Y. Kanazhevskaya, Alexey N. Masliy, Vladimir A. Kozlov. Chemical and biological properties of a supramolecular complex of tuftsin and cucurbit[7]uril. International Immunopharmacology 2017, 47 , 199-205. https://doi.org/10.1016/j.intimp.2017.03.032
    83. Zhaoxu Wang, Nicolay V. Tsarevsky. Well‐defined polymers containing high density of pendant viologen groups. Journal of Polymer Science Part A: Polymer Chemistry 2017, 55 (7) , 1173-1182. https://doi.org/10.1002/pola.28474
    84. Nianxing Wang, Zsófia Lukáacs, Bhushan Gadgil, Pia Damlin, Csaba Janáky, Carita Kvarnström. Electrochemical deposition of polyviologen-reduced graphene oxide nanocomposite thin films. Electrochimica Acta 2017, 231 , 279-286. https://doi.org/10.1016/j.electacta.2017.02.065
    85. Yingfeng Song, Xinghua Huang, Haojie Hua, Qiaochun Wang. The synthesis of a rigid conjugated viologen and its cucurbituril pseudorotaxanes. Dyes and Pigments 2017, 137 , 229-235. https://doi.org/10.1016/j.dyepig.2016.10.012
    86. J. Mohanty, S Dutta Choudhury, N. Barooah, H. Pal, A.C. Bhasikuttan. Mechanistic Aspects of Host–Guest Binding in Cucurbiturils: Physicochemical Properties. 2017, 435-457. https://doi.org/10.1016/B978-0-12-409547-2.11028-5
    87. Soumen K. Samanta, Kimberly G. Brady, Lyle Isaacs. Self-assembly of cucurbit[7]uril based triangular [4]molecular necklaces and their fluorescence properties. Chemical Communications 2017, 53 (18) , 2756-2759. https://doi.org/10.1039/C6CC10328F
    88. Jinglin Shen, Jinyu Pang, Guiying Xu, Xia Xin, Yingjie Yang, Xiaoyu Luan, Shiling Yuan. Smart stimuli-responsive fluorescent vesicular sensor based on inclusion complexation of cyclodextrins with Tyloxapol. RSC Advances 2016, 6 (14) , 11683-11690. https://doi.org/10.1039/C5RA26464B
    89. Nicolas Leblanc, Stephen Sproules, Karin Fink, Lionel Sanguinet, Olivier Alévêque, Eric Levillain, Patrick Rosa, Annie K. Powell. A fascinating multifaceted redox-active chelating ligand: introducing the N,N′-dimethyl-3,3′-biquinoxalinium “methylbiquinoxen” platform. Chemical Science 2016, 7 (6) , 3820-3828. https://doi.org/10.1039/C5SC04904K
    90. Zhaoxu Wang, Nicolay V. Tsarevsky. Well-defined polymers containing a single mid-chain viologen group: synthesis, environment-sensitive fluorescence, and redox activity. Polymer Chemistry 2016, 7 (26) , 4402-4410. https://doi.org/10.1039/C6PY00628K
    91. Sayeed Ashique Ahmed, Aninda Chatterjee, Banibrata Maity, Debabrata Seth. Supramolecular interaction of a cancer cell photosensitizer in the nanocavity of cucurbit[7]uril: A spectroscopic and calorimetric study. International Journal of Pharmaceutics 2015, 492 (1-2) , 103-108. https://doi.org/10.1016/j.ijpharm.2015.07.016
    92. Farah Benyettou, Katia Nchimi‐Nono, Mustapha Jouiad, Yoann Lalatonne, Irena Milosevic, Laurence Motte, John‐Carl Olsen, Na'il Saleh, Ali Trabolsi. Viologen‐Templated Arrays of Cucurbit[7]uril‐Modified Iron‐Oxide Nanoparticles. Chemistry – A European Journal 2015, 21 (12) , 4607-4613. https://doi.org/10.1002/chem.201405774
    93. Chengcheng Zhou, Xinhao Cheng, Qiang Zhao, Yun Yan, Jide Wang, Jianbin Huang. Self-Assembly of Channel Type β-CD Dimers Induced by Dodecane. Scientific Reports 2014, 4 (1) https://doi.org/10.1038/srep07533
    94. Giacomo Bergamini, Andrea Fermi, Marianna Marchini, Mirko Locritani, Alberto Credi, Margherita Venturi, Fabrizia Negri, Paola Ceroni, Massimo Baroncini. A Highly Luminescent Tetramer from a Weakly Emitting Monomer: Acid‐ and Redox‐Controlled Multiple Complexation by Cucurbit[7]uril. Chemistry – A European Journal 2014, 20 (23) , 7054-7060. https://doi.org/10.1002/chem.201400375
    95. Christian C. De Filippo, Hao Tang, Luca Ravotto, Giacomo Bergamini, Patrizio Salice, Miriam Mba, Paola Ceroni, Elena Galoppini, Michele Maggini. Synthesis and Electronic Properties of 1,2‐Hemisquarimines and Their Encapsulation in a Cucurbit[7]uril Host. Chemistry – A European Journal 2014, 20 (21) , 6412-6420. https://doi.org/10.1002/chem.201400039
    96. Maher Fathalla, Nathan L. Strutt, Jonathan C. Barnes, Charlotte L. Stern, Chenfeng Ke, J. Fraser Stoddart. Fluorescence Enhancement of a Porphyrin–Viologen Dyad by Pseudorotaxane Formation with Cucurbit[7]uril. European Journal of Organic Chemistry 2014, 2014 (14) , 2873-2877. https://doi.org/10.1002/ejoc.201402018
    97. Xu-Hui Jin, Cheng Chen, Cai-Xia Ren, Li-Xuan Cai, Jie Zhang. Bright white-light emission from a novel donor–acceptor organic molecule in the solid state via intermolecular charge transfer. Chem. Commun. 2014, 50 (100) , 15878-15881. https://doi.org/10.1039/C4CC07063A
    98. Shunwei Chen, Zhe Han, Dongju Zhang, Jinhua Zhan. Theoretical study of the inclusion complexation of TCDD with cucurbit[n]urils. RSC Adv. 2014, 4 (94) , 52415-52422. https://doi.org/10.1039/C4RA06011C
    99. Xin-Long Ni, Jun-Ming Yi, Sen Song, Yun-Qian Zhang, Sai-Feng Xue, Qian-Jiang Zhu, Zhu Tao. Supramolecular interactions of bisbenzimidazolyl derivatives with cucurbit[7]uril, potential axle molecules bearing a novel fluorescent signal response. Tetrahedron 2013, 69 (30) , 6219-6222. https://doi.org/10.1016/j.tet.2013.05.031
    100. Karel J. Hartlieb, Ashish N. Basuray, Chenfeng Ke, Amy A. Sarjeant, Henri‐Pierre Jacquot de Rouville, Takashi Kikuchi, Ross S. Forgan, Josh W. Kurutz, J. Fraser Stoddart. Chameleonic Binding of the Dimethyldiazaperopyrenium Dication by Cucurbit[8]uril. Asian Journal of Organic Chemistry 2013, 2 (3) , 225-229. https://doi.org/10.1002/ajoc.201200187
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