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Articles

Indole-based distinctive chemosensors for ‘naked-eye’ detection of CN and HSO4, associated with hydrogen-bonded complex and their DFT study

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Pages 239-248 | Received 03 Jun 2015, Accepted 06 Sep 2015, Published online: 11 Nov 2015

References

  • (a) Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419–447610.1021/cr010421e; (b) Caltagirone, C.; Gale, P.A. Chem. Soc. Rev. 2009, 38, 520–563; (c) Wiskur, S.L.; Ait-Haddou, H.; Lavigne, J.J.; Anslyn, E.V. Acc. Chem. Res. 2001, 34, 963–972; (d) Amendola, V.; Fabbrizzi, L. Chem. Commun. 2009, 513–531.
  • (a) Young, C.; Tidwell, L.; Anderson, C. Cyanide Social, Industrial, and Economic Aspects; Minerals, Metals, and Materials Society: Warrendale, PA, 2001; (b) Eisler, R. Cyanide Hazards to Fish, Wildlife, and Invertebrates: A 80 Synoptic Review – U.S. Fish Wildl. Serv., Biol. Rep. 1991, 85, 1–58.
  • (a) Baskin, S.I.; Brewer, T.G. In Medical Aspects of Chemical and Biological Warfare: Cyanide Poisoning (Chapter 10) Sidell, F.; Takafuji, E.T.; Franz, D.R. Eds.; TMM Publications: Washington, DC, 1997, 10, 271–286; (b) Holland, M.A.; Kozlowski, L.M. Clin. Pharm. 1986, 5, 737–741; (c) Way, J.L. Annu. Rev. Pharmacol. Toxicol. 1984, 24, 451–481.
  • (a) Kumar, S.; Singh, P.; Hundal, G.; Hundal, M.S.; Kumar, S. Chem. Commun. 2013, 49, 2667–266910.1039/c3cc40435h; (b) Mashraqui, S.H.; Betkar, R.; Chandiramani, M.; Estarellasb, C.; Fronterab, A. New J. Chem. 2011, 35, 57–60; (c) Lee, K.S.; Kim, H.J.; Kim, G.H.; Shin, I.; Hong, J.I. Org. Lett. 2008, 10, 49–51; (d) Li, M.-J.; Lin, Z.; Chen, X.; Chen, G. Dalton Trans. 2014, 43, 11745–11751; (e) Wang, F.; Wang, L.; Chen, X.; Yoon, J. Chem. Soc. Rev. 2014, 43, 4312–4324; (f) Garg, B.; Yan, L.; Bisht, T.; Zhu, C.; Ling, Y.-C. RSC Adv. 2014, 4, 36344–36349; (g) Khairnar, N.; Tayade, K.; Bothra, S.; Sahoo, S.K.; Singh, J.; Singh, N.; Bendre, R.; Kuwar, A. RSC Adv. 2014, 4, 41802–41806; (h) Wang, P.; Yao, Y.; Xue, M. Chem. Commun. 2014, 50, 5064–5067; (i) Zhang, Y.; Yu, D.; Feng, G. RSC Adv. 2014, 4, 14752–14757; (j) Peng, M.-J.; Guo, Y.; Yang, X.-F.; Suzenet, F.; Li, J.; Li, C.-W.; Duan, Y.-W. RSC Adv. 2014, 4, 19077–19085.
  • (a) Goswami, S.; Manna, A.; Paul, S.; Aich, K.; Das, A.K.; Chakraborty, S. Tetrahedron Lett. 2013, 54, 1785–178910.1016/j.tetlet.2012.12.092; (b) Saha, S.; Ghosh, A.; Mahato, P.; Mishra, S.; Mishra, S.K.; Suresh, E.; Das, S.; Das, A. Org. Lett. 2010, 12, 3406–3409; (c) Hao, Y.; Chen, W.; Wang, L.; Zhou, B.; Zang, Q.; Chen, S.; Liu, Y.-N. Anal. Methods 2014, 6, 2478–2483; (d) Lin, Y.-D.; Peng, Y.-S.; Su, W.; Tu, C.-H.; Sun, C.-H.; Chow, T.J. Tetrahedron 2012, 68, 2523–2526; (e) Dong, Y.-M.; Peng, Y.; Dong, M.; Wang, Y.-W. J. Org. Chem. 2011, 76, 6962–6966; (f) Xu, Z.; Chen, X.; Kim, H.N.; Yoon, J. Chem. Soc. Rev. 2010, 39, 127–137; (g) Huh, J.O.; Do, Y.; Lee, M.H. Organometallics 2008, 27, 1022–1025; (h) Konidena, R.K.; Thomas, K.R.J. RSC Adv. 2014, 4, 22902–22910.
  • (a) Xu, Z.; Chen, X.; Kim, H.N.; Yoon, J., Chem. Soc. Rev. 2010, 39, 127–137; (b) Kaur, K.; Saini, R.; Kumar, A.; Luxami, V.; Kaur, N.; Singh, P.; Kumar, S. Coord. Chem. Rev. 2012, 256, 1992–2028.
  • Moyer, B.A.; Delmau, L.H.; Fowler, C.J.; Ruas, A.; Bostick, D.A.; Sessler, J.L.; Katayeu, E.; Pantos, G.D.; Llinares, J.M.; Hossain, M.A.; Kang, S.O.; Bowman-James, K. Supramolecular Chemistry of Environmentally Relevant Anions: Advances in Inorganic Chemistry ed. Eldik, R.V.; Bowman-James, K., Academic Press: New York, 2006, 59, 175–204.
  • McKee, J.E.; Wolf, H.W. Water Quality Criteria, 2nd ed.; California State Water Quality Control Board: Sacramento, CA, 1963.
  • (a) Goswami, S.; Das, S.; Aich, K.; Sarkar, D.; Mondal, T.K. Tetrahedron Lett. 2013, 54, 6892–689610.1016/j.tetlet.2013.10.033; (b) Bhardwaj, V.K.; Saluja, P.; Hundal, G.; Hundal, M.S.; Singh, N.; Jang, D.O. Tetrahedron 2013, 69, 1606–1610; (c) Song, N.R.; Moon, J.H.; Choi, J.; Jun, E.J.; Kim, Y.; Kim, S.-J.; Lee, J.Y.; Yoon J. Chem. Sci. 2013, 4, 1765–1771; (d) Kaur, P.; Kaur, H.; Singh, K. Analyst 2013, 138, 425–428; (e) Yang, S.-T.; Liao, D.-J.; Chen, S.-J.; Hu, C.-H.; Wu, A.-T. Analyst 2012, 137, 1553–1555; (f) Sarkar, D.; Pramanik, A.K.; Mondal, T.K. RSC Adv. 2014, 4, 25341–25347; (g) Fegade, U.; Sahoo, S.K.; Singh, A.; Mahulikar, P.; Attarde, S.; Singh, N.; Kuwar, A. RSC Adv. 2014, 4, 15288–15292; (h) Kumar, V.; Kumar, A.; Diwan, U.; Upadhyay, K.K. Chem. Commun. 2012, 48, 9540–9542.
  • (a) Ali, H.D.P.; Kruger, P.E.; Gunnlaugsson, T. New J. Chem. 2008, 32, 1153–116110.1039/b715533f; (b) Lin, Z.H.; Ou, S.J.; Duan, C.Y.; Zhang, R.G.; Bai, Z.P. Chem. Commun. 2006, 624–626; (c) Hu, S.Z.; Guo, Y.; Xu, J.; Shao, S.J. Org. Biomol. Chem. 2008, 6, 2071–2075; (d) Lopez, M.V.; Bermejo, M.R.; Vazquez, M.E.; Taglietti, A.; Zaragoza, G.; Pedrido, R.; Martinez-Calvo, M. Org. Biomol. Chem. 2010, 8, 357–362.
  • (a) Li, Q.; Guo, Y.; Shao, S. Analyst 2012, 137, 4497–450110.1039/c2an35904a; (b) Hutt, J.T.; Jo, J.; Olasz, A.; Chen, C.-H.; Lee, D.; Aron, Z.D. Org. Lett. 2012, 14, 3162–3165; (c) Gale, P.A.; Hiscock, J.R.; Lalaoui, N.; Light, M.E.; Wells, N.J.; Wenzel, M. Org. Biomol. Chem. 2012, 10, 5909–5915; (d) Sakai, R.; Nagai, A.; Tago, Y.; Sato, S.; Nishimura, Y.; Arai, T.; Satoh, T.; Kakuchi, T. Macromolecules 2012, 45, 4122–4127; (e) Fu, L.; Jiang, F.-L.; Fortin, D.; Harvey, P.D.; Liu, Y. Chem. Commun. 2011, 47, 5503–5505.
  • (a) Gale, P.A. Chem. Commun. 2008, 4525–454010.1039/b809508f; (b) Shiraishi, Y.; Maehara, H.; Hirai, T. Org. Biomol. Chem. 2009, 7, 2072–2076; (c) Caltagirone, C.; Gale, P.A.; Hiscock, J.R.; Brooks, S.J.; Hursthouse, M.B.; Light, M.E. Chem. Commun. 2008, 3007–3009; (d) Dydio, P.; Zielinski, T.; Jurczak, J. Chem. Commun. 2009, 4560–4562.
  • (a) Wang, L.; He, X.; Guo, Y.; Xu, J.; Shao, S. Org. Biomol. Chem. 2011, 9, 752–75710.1039/C0OB00472C; (b) Wang, L.; Wei, W.; Guo, Y.; Xu, J.; Shao, S. Spectrochim. Acta Part A 2011, 78, 726–731; (c) He, X.; Hu, S.; Liu, K.; Guo, Y.; Xu, J.; Shao, S. Org. Lett. 2006, 8, 333–336; (d) Wei, W.; Guo, Y.; Xu, J.; Shao, S. Spectrochim. Acta Part A 2010, 77, 620–624.
  • (a) Dey, S.; Sain, D.; Goswami, S. RSC Adv. 2014, 4, 428–43310.1039/C3RA45197F; (b) Dey, S.; Sain, D. Supramol. Chem. 2014, 26, 769–776; (c) Dey, S.; Sain, D.; Kumar, A.; Kumari, C. RSC Adv. 2014, 4, 51486–51495.
  • (a) Mallegol, T.; Gmouh, S.; Meziane, M.A.A.; Blanchard-Desce, M.; Mongin, O. SynthSIs 2005, 1771–1774; (b) Fieser, L.F.; Hartwell, J.L.; Jones, J.E.; Wood, J.H.; Bost, R.W. Org. Syn. 1940, 20, 11–13.
  • (a) Hammud, H.H.; Ghannoum, A.; Masoud, M.S. Spectrochim. Acta. Part A 2006, 63, 255–26510.1016/j.saa.2005.04.020; (b) Sain, D.; Kumari, C.; Kumar, A.; Dey, S. Sens. Actuat. B 2015, 221, 849–856.
  • (a) Shortreed, M.; Kopelman, R.; Kuhn, M.; Hoyland, B. Anal. Chem. 1996, 68, 1414–141810.1021/ac950944k; (b) Lin, W.; Yuan, L.; Cao, Z.; Feng, Y.; Long, L. Chem. Eur. J. 2009, 15, 5096–5103; (c) Yang, Y.; Cheng, T.; Zhu, W.; Xu, Y.; Qian, X. Org. Lett. 2011, 13, 264–267; (d) Zhu, M.; Yuan, M.; Liu, X.; Xu, J.; Lv, J.; Huang, C.; Liu, H.; Li, Y.; Wang, S.; Zhu, D. Org. Lett. 2008, 10, 1481–1484.
  • (a) Mahapatra, A.K.; Hazra, G.; Sahoo, P. Beilstein J. Org. Chem. 2010, 6, 1–8; (b) Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Borsari, L.; Danesi, A.; Giorgi, C.; Lodeiro, C.; Mariani, P.; Pina, F.; Santarelli, S.; Tamayo, A.; Valtancoli, B. Dalton Trans. 2006, 4000-4010.
  • Job, P. Ann. Chim. 1928, 9, 113–203.
  • (a) Benesi, H.A.; Hildebrand, J.H. J. Am. Chem. Soc. 1949, 71, 2703–270710.1021/ja01176a030; (b) Liao, J.-H.; Chen, C.-T.; Chou, H.-C.; Cheng, C.-C.; Chou, P.-T.; Fang, J.-M.; Slanina, Z.; Chow, T.J. Org. Lett. 2002, 4, 3107–3110.
  • Frisch, M.J., et al. GAUSSIAN 09, Rev. D.01; Gaussian, Inc.: Wallingford, CT, 2009.
  • Dennington, R.D. (II), Keith, T.A.; Millam, J.M. GaussView 5.0, Gaussian, Inc.: Wallingford, CT, 2009.
  • (a) Becke, A.D. J. Chem. Phys. 1993, 98, 5648–565210.1063/1.464913; (b) Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B 1988, 37, 785–789; (c) Becke, A.D. Phys. Rev. A 1988, 38, 3098–3100.
  • Gu, R.; Van Snick, S.V.; Robeyns, K.; Van Meervelt, L.V.; Dehaen, W. Org. Biomol. Chem. 2009, 7, 380–385.10.1039/B815908D
  • Vahdat, S.M.; Khaksar, S.; Baghery, S. Lett. Org. Chem. 2012, 9, 138–144.10.2174/157017812800221690
  • Deb, M.L.; Baruah, B.; Bhuyan, P.J. Synthesis 2008, 286–292.

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