Table of Contents Author Guidelines Submit a Manuscript
Advances in Chemistry
Volume 2016, Article ID 6438187, 11 pages
http://dx.doi.org/10.1155/2016/6438187
Research Article

A BTT-Based Colorimetric Dual Sensor for Hg(II) and Selected Anions with Molecular Logic Operations

1Department of Chemistry and Biochemistry, University of Namibia, 340 Mandume Ndemufayo Avenue, Windhoek 9000, Namibia
2College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China

Received 27 February 2016; Accepted 16 May 2016

Academic Editor: Ipsita Banerjee

Copyright © 2016 Veikko Uahengo et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. J. H. Borroughes, D. D. C. Bradley, A. R. Brown et al., “Light-emitting diodes based on conjugated polymers,” Nature, vol. 347, pp. 539–541, 1990. View at Publisher · View at Google Scholar
  2. P. Garcia, J. Penuut, P. Hapiot et al., “Effect of end substitution on electrochemical and optical properties of oligothiophenes,” The Journal of Physical Chemistry, vol. 97, pp. 513–516, 1993. View at Google Scholar
  3. J. M. Tour, “Conjugated macromolecules of precise length and constitution. Organic synthesis for the construction of nanoarchitectures,” Chemical Reviews, vol. 96, no. 1, pp. 537–553, 1996. View at Publisher · View at Google Scholar · View at Scopus
  4. G. Horowitz, “Organic field-effect transistors,” Advanced Materials, vol. 10, no. 5, pp. 365–377, 1998. View at Publisher · View at Google Scholar · View at Scopus
  5. F. Cherionx and L. Guyard, “Synthesis and electrochemical properties of novel 1,3,5-tris(oligothienyl)benzenes: a new generation of 3D reticulating agents,” Advanced Funtional Materials, vol. 11, no. 4, pp. 305–309, 2001. View at Google Scholar · View at Scopus
  6. A. Facchetti, M.-H. Yoon, C. L. Stern, G. R. Hutchison, M. A. Ratner, and T. J. Marks, “Building blocks for N-type molecular and polymeric electronics. Perfluoroalkyl- versus alkyl-functionalized oligothiophenes (nTs; n=2-6). Systematic synthesis, spectroscopy, electrochemistry, and solid-state organization,” Journal of the American Chemical Society, vol. 126, no. 41, pp. 13480–13501, 2004. View at Publisher · View at Google Scholar · View at Scopus
  7. M. X. Chen, E. Perzon, N. Robisson et al., “Low band gap donor–acceptor–donor polymers for infra-red electroluminescence and transistors,” Synthetic Metals, vol. 146, no. 3, pp. 233–236, 2004. View at Publisher · View at Google Scholar · View at Scopus
  8. K. Mullen and U. Scherf, Organic light Emitting Devices, Synthesis, Properties and Applications, Wiley-VCH, New York, NY, USA, 2006.
  9. C. Brabec, V. Dyakonov, and U. Scherf, Eds., Organic Photovoltaic Materials, Device Physics and Manufacturing Technologies, Springer, Heidelberg, Germany, 2008.
  10. P. M. Beaujuge, S. Ellinger, and J. R. Reynolds, “The donor-acceptor approach allows ablack-to-transmissive switching polymeric electrochrome,” Nature Materials, vol. 7, no. 10, pp. 795–799, 2008. View at Publisher · View at Google Scholar · View at Scopus
  11. F. Cherionx and L. Guyard, “Synthesis and electrochemical properties of novel 1,3,5-tris(oligothienyl)benzenes: a new generation of 3D reticulating agents,” Advanced Funtional Materials, vol. 11, no. 4, pp. 305–309, 2001. View at Publisher · View at Google Scholar · View at Scopus
  12. Y. Nicolas, P. Blanchard, E. Levillain, M. Allain, N. Mercier, and J. Roncali, “Planarized star-shaped oligothiophenes with enhanced π-electron delocalization,” Organic Letters, vol. 6, no. 2, pp. 273–276, 2004. View at Publisher · View at Google Scholar · View at Scopus
  13. I. F. Perepichka and D. I. Perepichka, Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics, John Wiley & Sons, London, UK, 2009.
  14. P. M. Beaujuge, W. Pisula, N. T. Hoi, S. Ellinger, K. Müllen, and J. R. Reynolds, “Tailoring structure-property relationships in dithienosilole- benzothiadiazole donor-acceptor copolymers,” Journal of the American Chemical Society, vol. 131, no. 22, pp. 7514–7515, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. T. Taerum, O. Lukoyanova, R. G. Wylie, and D. F. Perepichka, “Synthesis, polymerization, and unusual properties of new star-shaped thiophene oligomers,” Organic Letters, vol. 11, no. 15, pp. 3230–3233, 2009. View at Publisher · View at Google Scholar · View at Scopus
  16. P. M. Beaujuge, J. Subbiah, K. R. Choudhury et al., “Green dioxythiophene-benzothiadiazole donor-acceptor copolymers for photovoltaic device applications,” Chemistry of Materials, vol. 22, no. 6, pp. 2093–2106, 2010. View at Publisher · View at Google Scholar · View at Scopus
  17. X. Guo, S. Wang, V. Enkelmann, M. Baumgarten, and K. Müllen, “Making benzotrithiophene a stronger electron donor,” Organic Letters, vol. 13, no. 22, pp. 6062–6065, 2011. View at Publisher · View at Google Scholar · View at Scopus
  18. T. Kashiki, M. Kohara, I. Osaka, E. Miyazaki, and K. Takimiya, “Synthesis and characterization of benzo[1, 2-b:3, 4-b′:5, 6-b]trithiophene (BTT) oligomers,” Journal of Organic Chemistry, vol. 76, no. 10, pp. 4061–4070, 2011. View at Publisher · View at Google Scholar
  19. K. M. N. De Silva, E. Hwang, W. K. Serem, F. R. Fronczek, J. C. Garno, and E. E. Nesterov, “Long-chain 3,4-ethylenedioxythiophene/thiophene oligomers and semiconducting thin films prepared by their electropolymerization,” ACS Applied Materials and Interfaces, vol. 4, no. 10, pp. 5430–5441, 2012. View at Publisher · View at Google Scholar · View at Scopus
  20. X. Guo, S. R. Puniredd, M. Baumgarten, W. Pisula, and K. Müllen, “Benzotrithiophene-based donor–acceptor copolymers with distinct supramolecular organizations,” Journal of the American Chemical Society, vol. 134, no. 20, pp. 8404–8407, 2012. View at Publisher · View at Google Scholar · View at Scopus
  21. T.-A. Liu, C. Prabhakar, J.-Y. Yu, C.-H. Chen, H.-H. Huang, and J.-S. Yang, “Star-shaped oligothiophenes containing an isotruxene core: synthesis, electronic properties, electropolymerization, and film morphology,” Macromolecules, vol. 45, no. 11, pp. 4529–4539, 2012. View at Publisher · View at Google Scholar · View at Scopus
  22. A. L. Dyer, M. R. Craig, J. E. Babiarz, K. Kiyak, and J. R. Reynolds, “Orange and red to transmissive electrochromic polymers based on electron-rich dioxythiophenes,” Macromolecules, vol. 43, no. 10, pp. 4460–4467, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. P. Sista, B. Xue, M. Wilson et al., “Influence of the alkyl substituents spacing on the solar cell performance of benzodithiophene semiconducting polymers,” Macromolecules, vol. 45, no. 2, pp. 772–780, 2012. View at Publisher · View at Google Scholar · View at Scopus
  24. D. Tyler McQuade, A. E. Pullen, and T. M. Swager, “Conjugated polymer-based chemical sensors,” Chemical Reviews, vol. 100, no. 7, pp. 2537–2574, 2000. View at Publisher · View at Google Scholar · View at Scopus
  25. S. W. Thomas III, K. Venkatesan, P. Müller, and T. M. Swager, “Dark-field oxidative addition-based chemosensing: new bis-cyclometalated Pt(II) complexes and phosphorescent detection of cyanogen halides,” Journal of the American Chemical Society, vol. 128, no. 51, pp. 16641–16648, 2006. View at Publisher · View at Google Scholar · View at Scopus
  26. F. Wang, H. Gu, and T. M. Swager, “Carbon nanotube/polythiophene chemiresistive sensors for chemical warfare agents,” Journal of the American Chemical Society, vol. 130, no. 16, pp. 5392–5393, 2008. View at Publisher · View at Google Scholar · View at Scopus
  27. D.-S. Kim and H. A. Kyo, “Fluorescence ‘turn-on’ sensing of carboxylate anions with oligothiophene-based o-(carboxamido)trifluoroacetophenones,” Journal of Organic Chemistry, vol. 73, no. 17, pp. 6831–6834, 2008. View at Publisher · View at Google Scholar · View at Scopus
  28. T. T. Steckler, X. Zhang, J. Hwang et al., “A spray-processable, low bandgap, and ambipolar donor—acceptor conjugatedpolymer,” Journal of the American Chemical Society, vol. 131, no. 8, pp. 2824–2826, 2009. View at Publisher · View at Google Scholar · View at Scopus
  29. K. K. Upadhyay, A. Kumar, R. K. Mishra, T. M. Fyles, S. Upadhyay, and K. Thapliyal, “Reversible colorimetric switching of thiophene hydrazone based on complementary IMP/INH logic functions,” New Journal of Chemistry, vol. 34, no. 9, pp. 1862–1866, 2010. View at Publisher · View at Google Scholar · View at Scopus
  30. S. L. A. Kumar, R. Tamilarasan, M. S. Kumar, and A. Sreekanth, “Bisthiocarbohydrazones as colorimetric and ‘turn on’ fluorescent chemosensors for selective recognition of fluoride,” Industrial and Engineering Chemistry Research, vol. 50, no. 22, pp. 12379–12383, 2011. View at Publisher · View at Google Scholar · View at Scopus
  31. L. Mosca, P. Koutnik, V. M. Lynch, G. V. Zyryanov, N. A. Esipenko, and P. Anzenbacher Jr., “Host-guest complexes of pentiptycene receptors display edge-to-face interaction,” Crystal Growth and Design, vol. 12, no. 12, pp. 6104–6109, 2012. View at Publisher · View at Google Scholar
  32. Y.-H. Qiao, H. Lin, and H.-K. Lin, “A novel colorimetric sensor for anions recognition based on disubstituted phenylhydrazone,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 59, no. 3-4, pp. 211–215, 2007. View at Publisher · View at Google Scholar · View at Scopus
  33. J. Li, H. Lin, P. Jiang, and H. Lin, “An optical and electrochemical anion sensor of F investigated by UV-vis, 1H NMR and cyclic voltammetry,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 62, no. 3-4, pp. 209–213, 2008. View at Publisher · View at Google Scholar · View at Scopus
  34. Y. Wang, H. Lin, J. Shao, Z.-S. Cai, and H.-K. Lin, “A phenylhydrazone-based indole receptor for sensing acetate,” Talanta, vol. 74, no. 5, pp. 1122–1125, 2008. View at Publisher · View at Google Scholar · View at Scopus
  35. J. Shao, Y. Qiao, H. Lin, and H.-K. Lin, “A C3-symmetric colorimetric anion sensor bearing hydrazone groups as binding sites,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 71, no. 5, pp. 1736–1740, 2009. View at Publisher · View at Google Scholar · View at Scopus
  36. J. Li, Y. Wang, H. Len, and H. Lin, “A novel, simple, colorimetric receptor based on 2′,4′- dinitrophenylhydrazone for acetate ion in organic medium,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 63, no. 3-4, pp. 281–285, 2009. View at Publisher · View at Google Scholar · View at Scopus
  37. X.-F. Shang and X.-F. Xu, “The anion recognition properties of hydrazone derivatives containing anthracene,” BioSystems, vol. 96, no. 2, pp. 165–171, 2009. View at Publisher · View at Google Scholar · View at Scopus
  38. P. Singh, J. Kaur, and W. Holzer, “Acridone based Cu2+–F/F–Cu2+ responsive ON/OFF key pad,” Sensors and Actuators B: Chemical, vol. 150, no. 1, pp. 50–56, 2010. View at Publisher · View at Google Scholar · View at Scopus
  39. C. N. Carroll, B. A. Coombs, S. P. McClintock et al., “Anion-dependent fluorescence in bis(anilinoethynyl)pyridine derivatives: switchable ON-OFF and OFF-ON responses,” Chemical Communications, vol. 47, no. 19, pp. 5539–5541, 2011. View at Publisher · View at Google Scholar · View at Scopus
  40. E. Manandhar and K. J. Wallace, “Host-guest chemistry of pyrene-based molecular receptors,” Inorganica Chimica Acta, vol. 381, no. 1, pp. 15–43, 2012. View at Publisher · View at Google Scholar · View at Scopus
  41. W. Lu, M. Zhang, K. Liu, B. Fan, Z. Xia, and L. Jiang, “A fluoride-selective colorimetric and fluorescent chemosensor and its use for the design of molecular-scale logic devices,” Sensors and Actuators B: Chemical, vol. 160, no. 1, pp. 1005–1010, 2011. View at Publisher · View at Google Scholar · View at Scopus
  42. Q. Li, Y. Yue, Y. Guo, and S. Shao, “Fluoride anions triggered ‘OFF–ON’ fluorescent sensor for hydrogen sulfate anions based on a BODIPY scaffold that works as a molecular keypad lock,” Sensors and Actuators B: Chemical, vol. 173, pp. 797–801, 2012. View at Publisher · View at Google Scholar · View at Scopus
  43. W. Lu, D. Chen, H. Jiang, L. Jiang, and Z. Shen, “Polymer-based fluoride-selective chemosensor: synthesis, sensing property, and its use for the design of molecular-scale logic devices,” Journal of Polymer Science, Part A: Polymer Chemistry, vol. 50, no. 3, pp. 590–598, 2012. View at Publisher · View at Google Scholar · View at Scopus
  44. V. Uahengo, B. Xiong, N. Zhou, P. Cai, K. Hu, and G. Cheng, “Synthesis of a phenylhydrazone-based colorimetric anion sensor with complementary IMP/INH logic functions,” Chinese Journal of Chemistry, vol. 30, no. 8, pp. 1702–1708, 2012. View at Publisher · View at Google Scholar · View at Scopus
  45. M. Ikeda, A. Matsu-Ura, S. Kuwahara, S. S. Lee, and Y. Habata, “Hg2+-sensing system based on structures of complexes,” Organic Letters, vol. 14, no. 6, pp. 1564–1567, 2012. View at Publisher · View at Google Scholar · View at Scopus
  46. J. Hu, T. Wu, G. Zhang, and S. Liu, “Highly selective fluorescence sensing of mercury ions over a broad concentration range based on mixed polymeric micelles,” Macromolecules, vol. 45, no. 9, pp. 3939–3947, 2012. View at Publisher · View at Google Scholar · View at Scopus
  47. L.-N. Neupane, P. Thirupathi, S. Jang, M. J. Jang, J. H. Kim, and K.-H. Lee, “Highly selectively monitoring heavy and transition metal ions by a fluorescent sensor based on dipeptide,” Talanta, vol. 85, no. 3, pp. 1566–1574, 2011. View at Publisher · View at Google Scholar · View at Scopus
  48. T. Li, Z. Yang, Y. Li, Z. Liu, G. Qi, and B. Wang, “A novel fluorescein derivative as a colorimetric chemosensor for detecting copper(II) ion,” Dyes and Pigments, vol. 88, no. 1, pp. 103–108, 2011. View at Publisher · View at Google Scholar · View at Scopus
  49. L. Tang, F. Li, M. Liu, and R. Nandhakumar, “Single sensor for two metal ions: colorimetric recognition of Cu2+ and fluorescent recognition of Hg2+,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 78, no. 3, pp. 1168–1172, 2011. View at Publisher · View at Google Scholar · View at Scopus
  50. H. Hart and M. Sasaoka, “Exocyclic benzenes. Synthesis and properties of benzo[1,2-c:3,4-c′:5,6-c]trithiophene, a tristhiahexaradialene,” Journal of the American Chemical Society, vol. 100, no. 13, pp. 4326–4327, 1978. View at Publisher · View at Google Scholar · View at Scopus