Investigation on the Property of the Excited State Intramolecular Proton Transfer Compounds and its Application as Fluorescence Chemical Sensor

doi:10.7517/j.issn.1674-0475.2013.05.335

Abstract

Abstract:

This article describes the development of the theoretical research about the excited state intramolecular proton transfer (ESIPT) compounds, and then several typical examples are presented to elaborate its application as fluorescence chemical sensor. This brief review may offer some help for the further research of ESIPT compounds.

Key words: excited state intramolecular proton transfer(ESIPT), isomerism, fluorescence probe, chemical sensor

CLC Number:

HU Rui, GUO Xu-dong, YANG Guo-qiang. Investigation on the Property of the Excited State Intramolecular Proton Transfer Compounds and its Application as Fluorescence Chemical Sensor[J]. Imaging Science and Photochemistry, 2013, 31(5): 335-348.

References

[1] Klymchenko A S, Demchenko A P. Electrochromic modulation of excited-state intramolecular proton transfer: the new principle in design of fluorescence sensors[J]. Journal of the American Chemical Society, 2002, 124: 12372-12379.

[2] Park S, Kwon J E, Kim S H, et al. A white-light-emitting molecule: frustrated energy transfer between constituent emitting centers[J]. Journal of the American Chemical Society, 2009, 131: 14043-14049.

[3] Sakai K, Tsuzuki T, Itoh Y, et al. Using proton-transfer laser dyes for organic laser diodes[J]. Applied Physics Letters, 2005, 86: 081103.

[4] Ma D G, Liang F S, Wang L X, et al. Blue organic light-emitting devices with an oxadiazole-containing emitting layer exhibiting excited state intramolecular proton transfer[J]. Chemical Physics Letters, 2002, 358: 24-28.

[5] Parejo P G, Zayat M, Levy D. Highly efficient UV-absorbing thin-film coatings for protection of organic materials against photodegradation[J]. Journal of Materials Chemistry, 2006, 16: 2165-2169.

[6] Cohen M D, Flavian S. Luminescence properties of N-salicylideneananiline and related anils in solution[J]. Journal of the Chemical Society B, 1967, 317.

[7] Sengupta P K, Kasha M. Excited state proton-transfer spectroscopy of 3-hytdroxyflavone and quercetin[J]. Chemical Physics Letters, 1979, 68: 382-385.

[8] Heller A, Williams D L. Intramolecular proton transfer reactions in excited fluorescent compounds[J]. The Journal of Physical Chemistry, 1970, 74: 4473-4480.

[9] Ikegami M,Arai T. Photoinduced intramolecular hydrogen atom transfer in 2-(2-hydroxyphenyl)benzoxazole and 2-(2-hydroxyphenyl)benzothiazole studied by laser flash photolysis[J]. Journal of the Chemical Society, Perkin Transactions 2, 2002: 1296-1301.

[10] Ding K, Courtney S J, Strandjord A J. Excited-state intramolecular proton transfer and vibrational relaxation in 2-(2-hydroxyphenyl)benzothiazole[J]. The Journal of Physical Chemistry, 1983, 87(7): 1184-1188.

[11] Barbara P F, Brus L E, Rentzepis P M. Intramolecular proton transfer and excited-state relaxation in 2-(2-hydroxyphenyl) benzothiazole[J]. Journal of the American Chemical Society, 1980, 102: 5631-5635.

[12] Aquino A J A, Lischka H, Hattig, C. Excited-state intramolecular proton transfer: a survey of TDDFT and RI-CC2 excited-state potential energy surfaces[J]. The Journal of Physical Chemistry A, 2005, 109(14): 3201-3208.

[13] Scheiner S, Kar T, C^uma M. Excited state intramolecular proton transfer in anionic analogues of malonaldehyde[J]. The Journal of Physical Chemistry A, 1997, 101(33): 5901-5909.

[14] Santra S, Krishnamoorthy G, Dogra S K. Excited-state intramolecular proton transfer in 2-(2'-acetamidophenyl)benzimidazole[J]. The Journal of Physical Chemistry A, 2000, 104(3): 476-482.

[15] Chou P T, Chen Y C, Yu W S. Excited-state intramolecular proton transfer in 10-hydroxybenzoquinoline[J]. The Journal of Physical Chemistry A, 2001, 105(10): 1731-1740.

[16] Hu R, Li S Y, Zeng Y, Chen J P, et al. Understanding the aggregation induced emission enhancement for a compound with excited state intramolecular proton transfer character[J]. Physical Chemistry Chemical Physics, 2011, 13: 2044-2051.

[17] Singla N, Chowdhury P. Density functional investigation of photo induced intramolecular proton transfer (IPT) in indole-7-carboxaldehyde and its experimental verification[J]. Journal of Molecular Structure, 2013, 1045: 72-80.

[18] Baughman B M, Stennett E, Lipner R E. Structural and spectroscopic studies of the photophysical properties of benzophenone derivatives[J]. The Journal of Physical Chemistry A, 2009, 113(28): 8011-8019.

[19] Gil M, Douhal A. Femtosecond dynamics of piroxicam structures in solutions[J]. The Journal of Physical Chemistry A, 2008, 112(36): 8231-8237.

[20] Henary M M, Wu Y G, Fahrni C J. Zinc(II)-selective ratiometric fluorescent sensors based on inhibition of excited-state intramolecular proton transfer[J]. Chemistry-A European Journal, 2004, 10(12): 3015-3025.

[21] Singh N, Kaur N, Mulrooney R C, Callan J F. A ratiometric fluorescent probe for magnesium employing excited state intramolecular proton transfer[J]. Tetrahedron Letters, 2008, 49(47): 6690-6692.

[22] Peng X J, Wu Y K, Fan J L, Tian M Z, Han K L. Colorimetric and ratiometric fluorescence sensing of fluoride: tuning selectivity in proton transfer[J]. Journal of Organic Chemistry, 2005, 70(25): 10524-10531.

[23] Yang X F, Qi H P, Wang L P, Su Z, Wang G. A ratiometric fluorescent probe for fluoride ion employing the excited-state intramolecular proton transfer[J]. Talanta, 2009, 80(1): 92-97.

[24] Wu Y K, Peng X J, Fan J L, et al. Fluorescence sensing of anions based on inhibition of excited-state intramolecular proton transfer[J]. Journal of Organic Chemistry, 2007, 72(1): 62-70.

[25] Chu Q, Medvetz D A, Pang Y. A polymeric colorimetric sensor with excited-state intramolecular proton transfer for anionic species[J]. Chemistry of Materials, 2007, 19(26): 6421-6429.

[26] Obare S O, Murphy C J. Selective blue emission from an HPBO-Li complex in alkaline media[J]. New Journal of Chemistry, 2001, 25: 1600-1604.

[27] Ma Q J, Zhang X B, Zhao X H, et al. A ratiometric fluorescent sensor for zinc ions based on covalently immobilized derivative of benzoxazole[J]. Spectrochimica Acta Part A, 2009, 73: 687-693.

[28] Xu Y Q, Pang Y. Zn²⁺ triggered excited-state intramolecular proton transfer: a sensitive probe with near-infrared emission from bis(benzoxazole) derivative[J]. Dalton Transactions, 2011, 40: 1503-1509.

[29] Bhalla V, Tejpal R, Kumar M. Terphenyl based fluorescent chemosensor for Cu²⁺ and F^- ions employing excited state intramolecular proton transfer[J]. Tetrahedron, 2011, 67: 1266-1271.

[30] Zhang X B, Cheng G, Zhang W J, et al. A fluorescent chemical sensor for Fe³⁺ based on blocking of intramolecular proton transfer of a quinazolinone derivative[J]. Talanta, 2007, 71: 171-177.

[31] Chan Y P, Fan L, You Q H, et al. Ratiometric pH responsive fluorescent probes operative on ESIPT[J]. Tetrahedron, 2013, 69: 5874-5879.

[32] Luo H Y, Zhang X B, He C L, et al. Synthesis of dipicolylamino substituted quinazoline as chemosensor for cobalt(II) recognition based on excited-state intramolecular proton transfer[J]. Spectrochimica Acta Part A, 2008, 70: 337-342.

[33] Han D Y, Kim J M, Kim J, et al. ESIPT-based anthraquinonylcalix 4 crown chemosensor for In³⁺[J]. Tetrahedron Letters, 2010, 51: 1947-1951.

[34] Goswami S, Manna A, Paul S, et al. Resonance-assisted hydrogen bonding induced nucleophilic addition to hamper ESIPT: ratiometric detection of cyanide in aqueous media[J]. Chemical Communications, 2013, 49: 2912-2914.

[35] Hu R, Feng J, Hu D H, et al. A rapid aqueous fluoride ion sensor with dual output modes[J]. Angewandte Chemie International Edition, 2010, 49: 4915-4918.

[36] Xiong L, Feng J, Hu R, et al. Sensing in 15 s for aqueous fluoride anion by water-insoluble fluorescent probe incorporating hydrogel[J]. Analytical Chemistry, 2013, 85: 4113-4119.

[37] Chen W H, Xing Y, Pang Y. A highly selective pyrophosphate sensor based on ESIPT turn-on in water[J]. Organic Letters, 2011, 13: 1362-1365.

[38] Chen S, Hou P, Zhou B J, et al. A red fluorescent probe for thiols based on 3-hydroxyflavone and its application in living cell imaging[J]. RSC Advances, 2013, 3: 11543-11546.

[39] Wang L Q, Zang Q G, Chen W S, et al. A ratiometric fluorescent probe with excited-state intramolecular proton transfer for benzoyl peroxide[J]. RSC Advances, 2013, 3: 8674-8676.

[40] Wang J F, Chu Q H, Liu X M, et al. Large fluorescence response by alcohol from a bis(benzoxazole)-zinc(II) complex: the role of excited state intramolecular proton transfer[J]. The Journal of Physical Chemistry B, 2013, 117: 4127-4133.

[41] Liang W R, Zhao Z, Zhang Y, et al. Highly selective detection of glutathione using a NIP/Cu²⁺ complex fluorescent probe[J]. Journal of Luminescence, 2012, 132: 1160-1165.

[42] McMorrow D, Kasha M. Proton-transfer spectroscopy of 3-hydroxychromones. Extreme sensitivity to hydrogen-bonding perturbations[J]. Journal of the American Chemical Society, 1983, 105: 5133-5134.

[43] Mordzinski A. Polyethylene as a medium for eliminating the solvent perturbation in intramolecular proton transfer systems[J]. Chemical Physics Letters, 1988, 150: 254-258.

[44] Klymchenko A S, Shvadchak V V, Yushchenko D A. Excited-state intramolecular proton transfer distinguishes microenvironments in single- and double-stranded DNA[J]. The Journal of Physical Chemistry B, 2008, 112:12050-12055.

[45] Strizhak A V, Postupalenko V Y, Shvadchak V V, et al. Two-color fluorescent L-amino acid mimic of tryptophan for probing peptide-nucleic acid complexes[J]. Bioconjugate Chemistry, 2012, 23: 2434-2443.