Advertisement

Pyrrole-Based Anion Sensors, Part I: Colorimetric Sensors

  • Pavel AnzenbacherJr.Email author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 24)

Abstract

This chapter focuses on chemo-sensing aspects of pyrrole and oligopyrrole-based colorimetric receptors for anions. Since pyrroles can play the role of a receptor as well as a signal transducer very efficiently and because of the focus on anion sensing, they can be organized following the modes of signal transduction such as colorimetry, fluorescence, and electrochemistry rather than structural features of the receptors. This chapter focuses on colorimetric sensors and in particular those based on pyrrole, polypyrrole, and pyrrole benzo-analogs, i.e., indole and carbazole-based sensors for anions.

Keywords

Anions Electrochemistry Fluroescence Luminescence Sensor 

References

  1. 1.
    Sessler JL, Gale PA, Cho W (2006) Anion Receptor Chemistry; Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 2006Google Scholar
  2. 2.
    Cho WS, Sessler JL (2005) Artificial pyrrole-based anion receptors. In: Schrader T, Hamiltonz AD (eds) Functional synthetic receptors. Wiley-VCH, WeinheimGoogle Scholar
  3. 3.
    Sessler JL, Camiolo S, Gale PA (2003) Coord Chem Rev 240:17–55CrossRefGoogle Scholar
  4. 4.
    Gale PA, Quesada R (2006) Coord Chem Rev 250:3219–3244CrossRefGoogle Scholar
  5. 5.
    Gale PA, Garcia-Garrido SE, Garric J (2008) Chem Soc Rev 37:151–190CrossRefGoogle Scholar
  6. 6.
    Caltagirone C, Gale PA (2009) Chem Soc Rev 38:520–563CrossRefGoogle Scholar
  7. 7.
    Beer PD, Gale PA (2001) Angew Chem Int Ed 40:486–516CrossRefGoogle Scholar
  8. 8.
    Sessler JL, Weghorn SJ (1997) Expanded, contracted & isomeric porphyrins. Tetrahedron organic chemistry series, vol 15. Pergamon, Oxford, UKGoogle Scholar
  9. 9.
    Sessler JL, Seidel D (2003) Angew Chem Int Ed, Oxford, UK, 42:5134–5175CrossRefGoogle Scholar
  10. 10.
    Sessler JL, Davis JM, Král V, Kimbrough T, Lynch V (2003) Org Biomol Chem 1:4113–4123CrossRefGoogle Scholar
  11. 11.
    Sessler JL, Davis JM (2001) Acc Chem Res 34:989–997CrossRefGoogle Scholar
  12. 12.
    Král V, Sessler JL, Zimmerman RS, Seidel D, Lynch V, Andrioletti B (2000) Angew Chem Int Ed 39:1055–1058CrossRefGoogle Scholar
  13. 13.
    Sessler JL, Zimmerman RS, Bucher C, Král V, Andrioletti B (2001) Pure Appl Chem 73:1041–1057CrossRefGoogle Scholar
  14. 14.
    Koehler T, Seidel D, Lynch V, Arp FO, Ou Z, Kadish KM, Sessler JL (2003) J Am Chem Soc 125:6872–6873CrossRefGoogle Scholar
  15. 15.
    Seidel D, Lynch V, Sessler JL (2002) Angew Chem Int Ed 41:1422–1425CrossRefGoogle Scholar
  16. 16.
    Carvlin MJ, Fiel RJ (1983) Nucl Acids Res 11:6121–6139CrossRefGoogle Scholar
  17. 17.
    Fiel RJ, Howard JC, Mark EH (1979) Datta Gupta N. Nucl Acids Res 6:3093–3118CrossRefGoogle Scholar
  18. 18.
    Fiel RJ, Munson BR (1980) Nucl Acids Res 8:2835–2842CrossRefGoogle Scholar
  19. 19.
    Pasternack RF, Gibbs EJ, Villafranca JJ (1983) Biochem 22:5409–5417CrossRefGoogle Scholar
  20. 20.
    Pasternack RF, Antebi A, Ehrlich B, Sidney D, Gibbs EJ, Bassner SL, Depoy LM (1984) J Mol Catal 23:235–242CrossRefGoogle Scholar
  21. 21.
    Takeuchi M, Shioya T, Swager TM (2001) Angew Chem Int Ed 40:3372–3376CrossRefGoogle Scholar
  22. 22.
    Schumacher AL, Hill P, Ariga K, D’Souza F (2007) Electrochem Commun 9:2751–2754CrossRefGoogle Scholar
  23. 23.
    Gupta I, Frohlich R, Ravikanth M (2008) Eur J Org Chem 11:1884–1900CrossRefGoogle Scholar
  24. 24.
    Sessler JL, Cyr MJ, Lynch V, McGhee E, Ibers JA (1990) J Am Chem Soc 112:2810–2813CrossRefGoogle Scholar
  25. 25.
    Shionoya M, Furuta H, Lynch V, Harriman A, Sessler JL (1992) J Am Chem Soc 114:5714–5722CrossRefGoogle Scholar
  26. 26.
    Furuta H, Cyr MJ, Sessler JL (1991) J Am Chem Soc 113:6677–6678CrossRefGoogle Scholar
  27. 27.
    Sessler JL, Ford DA, Cyr MJ, Furuta H (1991) J Chem Soc Chem Commun 1733–1735Google Scholar
  28. 28.
    Sessler JL, Cyr MJ, Burrell AK (1991) Synlett 127–134Google Scholar
  29. 29.
    Sessler JL, Mody TD, Ford DA, Lynch VM (1992) Angew Chem Int Ed 31:452–455CrossRefGoogle Scholar
  30. 30.
    Sessler JL, Morishima T, Lynch VM (1991) Angew Chem Int Ed 30:977–980CrossRefGoogle Scholar
  31. 31.
    Bauer VJ, Clive DLJ, Dolphin D, Paine JB III, Harris FL, King MM, Loder J, Wang SWC, Woodward RB (1983) J Am Chem Soc 105:6429–6436CrossRefGoogle Scholar
  32. 32.
    Král V, Furuta H, Shreder K, Lynch VM, Sessler JL (1996) J Am Chem Soc 118:1595–1607CrossRefGoogle Scholar
  33. 33.
    Iverson BL, Shreder K, Král V, Lynch VM, Sessler JL (1996) J Am Chem Soc 118:1608–1616CrossRefGoogle Scholar
  34. 34.
    Král V, Sessler JL (1995) Tetrahedron 51:539–554CrossRefGoogle Scholar
  35. 35.
    Gorden AEV, Davis J, Sessler JL, Král V, Webster KD, Schroeder NL (2004) Supramol Chem 16:91–100CrossRefGoogle Scholar
  36. 36.
    Sessler JL, Andrievsky A, Král V, Lynch VM (1997) J Am Chem Soc 119:9385–9392CrossRefGoogle Scholar
  37. 37.
    Baeyer A (1886) Dtsch Chem Ges 19:2184–2185CrossRefGoogle Scholar
  38. 38.
    Gale PA, Sessler JL, Král V, Lynch VM (1996) J Am Chem Soc 118:5140–5141CrossRefGoogle Scholar
  39. 39.
    Camiolo S, Coles SJ, Gale PA, Hursthouse MB, Sessler JL (2001) Acta Cryst E57:o816–o818Google Scholar
  40. 40.
    Anzenbacher P Jr, Try AC, Miyaji H, Jursíková K, Lynch VM, Marquez M, Sessler JL (2000) J Am Chem Soc 122:10268–10272CrossRefGoogle Scholar
  41. 41.
    Sessler JL, Gross DE, Cho WS, Lynch VM, Schmidtchen FP, Bates GW, Light ME, Gale PA (2006) J Am Chem Soc 128:12281–12288CrossRefGoogle Scholar
  42. 42.
    Miyaji H, Sato W, Sessler JL (2000) Angew Chem Int Ed 39:1777–1780CrossRefGoogle Scholar
  43. 43.
    Nishiyabu R, Anzenbacher P Jr (2005) J Am Chem Soc 127:8270–8271CrossRefGoogle Scholar
  44. 44.
    Anzenbacher P Jr, Jursíková K, Shriver JA, Miyaji H, Lynch VM, Sessler JL, Gale PA (2000) J Org Chem 65:7641–7645CrossRefGoogle Scholar
  45. 45.
    Marshall WJ, Bangert SK (2004) Clinical chemistry, 5th edn. Elsevier, EdinburgGoogle Scholar
  46. 46.
    Schmidt RF, Thews G (1989) Human physiology, 2nd edn. Springer, BerlinGoogle Scholar
  47. 47.
    Hong SJ, Yoo J, Kim SH, Kim JS, Yoon J, Lee CH (2009) Chem Commun 189–191Google Scholar
  48. 48.
    Lee CH, Miyaji H, Yoon DW, Sessler JL (2008) Chem Commun 24–34Google Scholar
  49. 49.
    Kim SH, Hong SJ, Yoo J, Kim SK, Sessler JL, Lee CH (2009) Org Lett 11:3626–3629CrossRefGoogle Scholar
  50. 50.
    Yoo J, Kim MS, Hong SJ, Sessler JL, Lee CH (2009) J Org Chem 74:1065–1069CrossRefGoogle Scholar
  51. 51.
    Nishiyabu R, Palacios MA, Dehaen W, Anzenbacher P Jr (2006) J Am Chem Soc 128: 11496–11504CrossRefGoogle Scholar
  52. 52.
    Gu R, Depraetere S, Kotek J, Budka J, Wagner-Wysiecka E, Biernat JF, Dehaen W (2005) Org Biomol Chem 3:2921–2923CrossRefGoogle Scholar
  53. 53.
    Depraetere S, Smet M, Dehaen W (1999) Angew Chem Int Ed 38:3359–3361CrossRefGoogle Scholar
  54. 54.
    Palacios MA, Nishiyabu R, Marquez M, Anzenbacher P Jr (2007) J Am Chem Soc 129: 7538–7544CrossRefGoogle Scholar
  55. 55.
    Lavigne JJ, Savoy S, Clevenge MB, Ritchie JE, McDoniel B, Yoo SJ, Anslyn EV, McDevitt JT, Shear JB, Neikirk D (1998) J Am Chem Soc 120:6429–6430CrossRefGoogle Scholar
  56. 56.
    Goodey A, Lavigne JJ, Savoy SM, Rodriguez MD, Curey T, Tsao A, Simmons G, Wright J, Yoo SJ, Sohn Y, Anslyn EV, Shear JB, Neikirk DP, McDevitt JT (2001) J Am Chem Soc 123:2559–2570CrossRefGoogle Scholar
  57. 57.
    Legin A, Smirnova A, Rudnitskaya A, Lvova L, Suglobova E, Vlasov Y (1999) Anal Chim Acta 385:131–135CrossRefGoogle Scholar
  58. 58.
    DiNatale C, Davide F, Brunink JAJ, D’Amico A, Vlasov YG, Legin AV, Rudnitskaya AM (1996) Sens Actuators B 34:539–542CrossRefGoogle Scholar
  59. 59.
    Gale PA, Twyman LJ, Handlin CI, Sessler JL (1999) Chem Commun 1851–1852Google Scholar
  60. 60.
    Shao S, Guo Y, He L, Jiang S, Yu X (2003) Tetrahedron Lett 44:2175–2178CrossRefGoogle Scholar
  61. 61.
    Linn MM, Poncio DC, Machado VG (2007) Tetrahedron Lett 48:4547–4551CrossRefGoogle Scholar
  62. 62.
    Saki N, Akkaya EU (2005) J Inclusion Phenom Macrocycl Chem 53:269–273CrossRefGoogle Scholar
  63. 63.
    Oddo B (1911) Gazz Chim Ital 41:248–255Google Scholar
  64. 64.
    Behr D, Brandänge S, Lindström B (1973) Acta Chem Scand 27:2411–2414CrossRefGoogle Scholar
  65. 65.
    Black CB, Andrioletti B, Try AC, Ruiperez C, Sessler JL (1999) J Am Chem Soc 121:10438–10439CrossRefGoogle Scholar
  66. 66.
    Pietrzak M, Try AC, Andrioletti B, Sessler JL, Anzenbacher P Jr, Limbach HH (2008) Angew Chem 120:1139–1142CrossRefGoogle Scholar
  67. 67.
    Mizuno T, Wei WH, Eller LR, Sessler JL (2002) J Am Chem Soc 124:1134–1135CrossRefGoogle Scholar
  68. 68.
    Anzenbacher P Jr, Tyson DS, Jursíková K, Castellano FN (2002) J Am Chem Soc 124:6232–6233CrossRefGoogle Scholar
  69. 69.
    Sessler JL, Maeda H, Mizuno T, Lynch VM, Furuta H (2002) Chem Commun 862–863Google Scholar
  70. 70.
    Sessler JL, Pantos DL, Katayev E, Lynch VM (2003) Org Lett 5:4141–4144CrossRefGoogle Scholar
  71. 71.
    Sessler JL, Maeda H, Mizuno T, Lynch VM, Furuta H (2002) J Am Chem Soc 124:13474–13479CrossRefGoogle Scholar
  72. 72.
    Sessler JL, Cho DG, Lynch V (2006) J Am Chem Soc 128:16518–16519CrossRefGoogle Scholar
  73. 73.
    Lin Z, Chen HC, Sun SS, Hsu CP, Chow TJ (2009) Tetrahedron 65:5216–5221CrossRefGoogle Scholar
  74. 74.
    Camiolo S, Gale PA, Hursthouse MB, Light ME (2003) Org Biomol Chem 1:741–744CrossRefGoogle Scholar
  75. 75.
    Chang KJ, Moon D, Lah MS, Jeong KS (2005) Angew Chem Int Ed 44:7926–7929CrossRefGoogle Scholar
  76. 76.
    Lee JY, Lee MH, Jeong KS (2007) Supramol Chem 19:257–263CrossRefGoogle Scholar
  77. 77.
    Chang KJ, Chae MK, Lee C, Lee JY, Jeong KS (2006) Tetrahedron Lett 47:6385–6388CrossRefGoogle Scholar
  78. 78.
    Kim NK, Chang KJ, Moon D, Lah MS, Jeong KS (2007) Chem Commun 3401–3403Google Scholar
  79. 79.
    Curiel D, Cowley A, Beer PD (2005) Chem Commun 236–238Google Scholar
  80. 80.
    Katayev EA, Boev NV, Khrustalev VN, Ustynyuk YA, Tananaev IG, Sessler JL (2007) J Org Chem 72:2886–2896CrossRefGoogle Scholar
  81. 81.
    Katayev EA, Sessler JL, Khrustalev VN, Ustynyuk YA (2007) J Org Chem 72:7244–7252CrossRefGoogle Scholar
  82. 82.
    Sessler JL, Katayev EA, Pantos GD, Reshetova MD, Khrustalev VN, Lynch VM, Ustynyuk YA (2005) Angew Chem Int Ed 44:7386–7390CrossRefGoogle Scholar
  83. 83.
    Amendola V, Esteban-Gomez D, Fabbrizzi L, Licchelli M (2006) Acc Chem Res 39:343–353CrossRefGoogle Scholar
  84. 84.
    Caltagirone C, Mulas A, Isaia F, Lippolis V, Gale PA, Light ME (2009) Chem Commun 6279–6281Google Scholar
  85. 85.
    Chen CL, Lin TP, Chen YS, Sun SS (2007) Eur J Org Chem 3999–4010Google Scholar
  86. 86.
    Chauhan SMS, Bisht T, Garg B (2009) Sens Actuators B Chem B141:116–123CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  1. 1.Department of Chemistry and Center for Photochemical SciencesBowling Green State UniversityBowling GreenUSA

Personalised recommendations