Journal of Fluorescence

, Volume 27, Issue 2, pp 745–754 | Cite as

TD-DFT Study of Absorption and Emission Spectra of 2-(2′-Aminophenyl)benzothiazole Derivatives in Water

  • Natthaporn Manojai
  • Rathawat Daengngern
  • Khanittha Kerdpol
  • Nawee Kungwan
  • Chanisorn Ngaojampa
ORIGINAL ARTICLE
First Online:
Received:
Accepted:

Abstract

Reduction of aromatic azides to amines is an important property of hydrogen sulphide (H2S) which is useful in fluorescence microscopy and H2S probing in cells. The aim of this work is to study the substituent effect on the absorption and emission spectra of 2-(2′-aminophenyl)benzothiazole (APBT) in order to design APBT derivatives for the use of H2S detection. Absorption and emission spectra of APBT derivatives in aqueous environment were calculated using density functional theory (DFT) and time-dependent DFT (TD-DFT) at B3LYP/6-311+G(d,p) level. The computed results favoured the substitution of strong electron-donating group on the phenyl ring opposite to the amino group for their large Stokes’ shifts and emission wavelengths of over 600 nm. Also, three designed compounds were suggested as potential candidates for the fluorescent probes. Such generalised guideline learnt from this work can also be useful in further designs of other fluorescent probes of H2S in water.

Keywords

Fluorescent probe 2-(2′-aminophenyl)benzothiazole Hydrogen sulfide Time-dependent density functional theory 
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Notes

Acknowledgements

This research is financially sponsored by the Research Administration Office, Graduate School of Chiang Mai University and Thailand Research Fund (MRG5980189 and RSA5880057) for the financial support.

References

  1. 1.
    Wang R et al (2012) Sensitive near-infrared fluorescent probes for thiols based on Se-N bond cleavage: imaging in living cells and tissues. Chem Eur J 18(36):11343–11349CrossRefPubMedGoogle Scholar
  2. 2.
    Yu F, Han X, Chen L (2014) Fluorescent probes for hydrogen sulfide detection and bioimaging. Chem Commun 50(82):12234–12249CrossRefGoogle Scholar
  3. 3.
    Kamoun P (2004) Endogenous production of hydrogen sulfide in mammals. Amino Acids 26(3):243–254CrossRefPubMedGoogle Scholar
  4. 4.
    Abe K, Kimura H (1996) The possible role of hydrogen sulfide as an endogenous neuromodulator. J Neurosci 16(3):1066–1071PubMedGoogle Scholar
  5. 5.
    Hosoki R, Matsuki N, Kimura H (1997) The possible role of hydrogen sulfide as an endogenous smooth muscle relaxant in synergy with nitric oxide. Biochem Biophys Res Commun 237(3):527–531CrossRefPubMedGoogle Scholar
  6. 6.
    Madden JA et al (2012) Precursors and inhibitors of hydrogen sulfide synthesis affect acute hypoxic pulmonary vasoconstriction in the intact lung. J Appl Physiol 112(3):411–418CrossRefPubMedGoogle Scholar
  7. 7.
    Tripatara P et al (2009) Characterisation of cystathionine gamma-lyase/hydrogen sulphide pathway in ischaemia/reperfusion injury of the mouse kidney: an in vivo study. Eur J Pharmacol 606(1–3):205–209CrossRefPubMedGoogle Scholar
  8. 8.
    Wang P et al (2011) Hydrogen sulfide and asthma. Exp Physiol 96(9):847–852CrossRefPubMedGoogle Scholar
  9. 9.
    Paul BD, Snyder SH (2012) H2S signalling through protein sulfhydration and beyond. Nat Rev Mol Cell Biol 13(8):499–507CrossRefPubMedGoogle Scholar
  10. 10.
    Lin VS, Chang CJ (2012) Fluorescent probes for sensing and imaging biological hydrogen sulfide. Curr Opin Chem Biol 16(5–6):595–601CrossRefPubMedPubMedCentralGoogle Scholar
  11. 11.
    Sivakumar K et al (2004) A fluorogenic 1,3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes. Org Lett 6(24):4603–4606CrossRefPubMedGoogle Scholar
  12. 12.
    Zhou Z, Fahrni CJ (2004) A fluorogenic probe for the copper(I)-catalyzed azide − alkyne ligation reaction: modulation of the fluorescence emission via 3(n, π*) − (π, π*) inversion. J Am Chem Soc 126(29):8862–8863CrossRefPubMedGoogle Scholar
  13. 13.
    Xie F et al (2008) A fluorogenic ‘click’ reaction of azidoanthracene derivatives. Tetrahedron 64(13):2906–2914CrossRefGoogle Scholar
  14. 14.
    Das SK et al (2012) A small molecule two-photon probe for hydrogen sulfide in live tissues. Chem Commun 48(67):8395–8397CrossRefGoogle Scholar
  15. 15.
    Bailey TS, Pluth MD (2013) Chemiluminescent detection of enzymatically produced hydrogen sulfide: substrate hydrogen bonding influences selectivity for H2S over biological thiols. J Am Chem Soc 135(44):16697–16704CrossRefPubMedGoogle Scholar
  16. 16.
    Wang C et al (2011) Tuning the optical properties of BODIPY dye through Cu(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Sci China Chem 55(1):125–130CrossRefGoogle Scholar
  17. 17.
    Huo F-J et al (2015) Highly selective fluorescent and colorimetric probe for live-cell monitoring of sulphide based on bioorthogonal reaction. Sci Rep 5:8969CrossRefPubMedPubMedCentralGoogle Scholar
  18. 18.
    Jiajin Z et al (2006) Two-photon-induced excited state intramolecular proton transfer process and nonlinear optical properties of HBT in cyclohexane solution. J Opt A Pure Appl Opt 8(10):835CrossRefGoogle Scholar
  19. 19.
    Rodembusch FS et al (2005) The first silica aerogels fluorescent by excited state intramolecular proton transfer mechanism (ESIPT). J Mater Chem 15(15):1537–1541CrossRefGoogle Scholar
  20. 20.
    Wang R et al (2009) Substituent and solvent effects on excited state intramolecular proton transfer in novel 2-(2′-hydroxyphenyl)benzothiazole derivatives. J Photochem Photobiol A Chem 205(1):61–69CrossRefGoogle Scholar
  21. 21.
    Arthen-Engeland T et al (1992) Singlet excited-state intramolecular proton tranfer in 2-(2 t’-hydroxyphenyl) benzoxazole: spectroscopy at low temperatures, femtosecond transient absorption, and MNDO calculations. Chem Phys 163(1):43–53CrossRefGoogle Scholar
  22. 22.
    Das K et al (1994) Excited-state intramolecular proton transfer in 2-(2-hydroxyphenyl)benzimidazole and -benzoxazole: effect of rotamerism and hydrogen bonding. J Phys Chem 98(37):9126–9132CrossRefGoogle Scholar
  23. 23.
    Daengngern R, Kungwan N (2015) Electronic and photophysical properties of 2-(2′-hydroxyphenyl)benzoxazole and its derivatives enhancing in the excited-state intramolecular proton transfer processes: a TD-DFT study on substitution effect. J Lumin 167:132–139CrossRefGoogle Scholar
  24. 24.
    Dogra SK (2005) Spectral characteristics of 2-(3′,5′-diaminophenyl)benzothiazole: effects of solvents and acid–base concentrations. J Photochem Photobiol A Chem 172(2):185–195CrossRefGoogle Scholar
  25. 25.
    Dey JK, Dogra SK (1991) Solvatochromism and Prototropism in 2-(Aminophenyl)benzothiazoles. Bull Chem Soc Jpn 64(10):3142–3152CrossRefGoogle Scholar
  26. 26.
    Jiang Y, Wu Q, Chang X (2014) A ratiometric fluorescent probe for hydrogen sulfide imaging in living cells. Talanta 121:122–126CrossRefPubMedGoogle Scholar
  27. 27.
    Zhang J, Guo W (2014) A new fluorescent probe for gasotransmitter H2S: high sensitivity, excellent selectivity, and a significant fluorescence off-on response. Chem Commun 50(32):4214–4217CrossRefGoogle Scholar
  28. 28.
    Becke AD (1993) A new mixing of Hartree–Fock and local density‐functional theories. J Chem Phys 98(2):1372–1377CrossRefGoogle Scholar
  29. 29.
    Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37(2):785–789CrossRefGoogle Scholar
  30. 30.
    Miehlich B et al (1989) Results obtained with the correlation energy density functionals of becke and Lee Yang and Parr. Chem Phys Lett 157(3):200–206CrossRefGoogle Scholar
  31. 31.
    Matsuzawa NN et al (2001) Time-dependent density functional theory calculations of photoabsorption spectra in the vacuum ultraviolet region. J Phys Chem A 105(20):4953–4962CrossRefGoogle Scholar
  32. 32.
    Jacquemin D et al (2006) Time-dependent density functional theory investigation of the absorption, fluorescence, and phosphorescence spectra of solvated coumarins. J Chem Phys 125(16):164324CrossRefPubMedGoogle Scholar
  33. 33.
    Chibani S et al (2012) On the computation of adiabatic energies in Aza-Boron-dipyrromethene dyes. J Chem Theory Comput 8(9):3303–3313CrossRefPubMedGoogle Scholar
  34. 34.
    Houari Y, Jacquemin D, Laurent AD (2013) TD-DFT study of the for coumarins. Chem Phys Lett 583:218–221CrossRefGoogle Scholar
  35. 35.
    Zakrzewska A et al (2013) Substituent effects on the photophysical properties of fluorescent 2-benzoylmethylenequinoline difluoroboranes: a combined experimental and quantum chemical study. Dyes Pigments 99(3):957–965CrossRefGoogle Scholar
  36. 36.
    Laurent AD, Adamo C, Jacquemin D (2014) Dye chemistry with time-dependent density functional theory. Phys Chem Chem Phys 16(28):14334–14356CrossRefPubMedGoogle Scholar
  37. 37.
    Tseng H-W et al (2015) Harnessing excited-state intramolecular proton-transfer reaction via a series of amino-type hydrogen-bonding molecules. J Phys Chem Lett 6(8):1477–1486CrossRefPubMedGoogle Scholar
  38. 38.
    Chen C-L et al (2016) Insight into the amino-type excited-state intramolecular proton transfer cycle using N-tosyl derivatives of 2-(2′-Aminophenyl)benzothiazole. J Phys Chem A 120(7):1020–1028CrossRefPubMedGoogle Scholar
  39. 39.
    Becke AD (1993) Density‐functional thermochemistry. III. The role of exact exchange. J Chem Phys 98(7):5648–5652CrossRefGoogle Scholar
  40. 40.
    Stephens PJ et al (1994) Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 98(45):11623–11627CrossRefGoogle Scholar
  41. 41.
    Adamo C, Barone V (1999) Toward reliable density functional methods without adjustable parameters: the PBE0 model. J Chem Phys 110(13):6158–6170CrossRefGoogle Scholar
  42. 42.
    Zhao YT, Truhlar DG (2006) Density functional for spectroscopy: No long-range self-interaction error, good performance for Rydberg and charge-transfer states, and better performance on average than B3LYP for ground states. J Phys Chem A 110:13126–13130CrossRefPubMedGoogle Scholar
  43. 43.
    O’boyle NM, Tenderholt AL, Langner KM (2007) cclib: a library, f.p.-i.c.c. algorithms. J Comput Chem 29(5):839–845CrossRefGoogle Scholar
  44. 44.
    Frisch MJ et al (2010) Gaussian 09 revisions C.01 & B.01. Gaussian, Inc., WallingfordGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceChiang Mai UniversityChiang MaiThailand

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