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Fluorescent Properties of 8-Substituted BODIPY Dyes: Influence of Solvent Effects

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Abstract

Three boron-dipyrrine (BODIPY) based dyes with bulky substituents in 8-position of dipyrrin ligand have been synthesized and characterized. Photophysical properties of the obtained compounds have been investigated in different individual solvents and solvent mixtures. Investigated compounds was found to be intensive fluorescent molecular rotors. The influence of different solvent parameters and the substituent nature on rotor characteristics have been observed and discussed. Minor changes in the nature of 8-substituent does not influence the spectral properties, but the presence of nitrogen donor atom in the phenyl substituent could be used for the sensing of the donor-acceptor interactions with solvent or dissolved compounds. The new approach of spectral properties correlation with solvent parameters was proposed, the viscosity parameter should be taken into account in case of BODIPYs with bulky substituents. The intensity of fluorescence molecular rotor properties decrease gradually with the viscosity increase above 1 cP.

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References

  1. Wang LY, Fang GP, Cao DR (2015) A novel phenol-based BODIPY chemosensor for selective detection Fe3+ with colorimetric and fluorometric dual-mode. Sensors Actuators B Chem 207:849–857

    Article  CAS  Google Scholar 

  2. He Y, Feng RK, Yi YR, Liu ZX (2014) Recent progress in the research of borondipyrromethene-based fluorescent ion chemosensor. Chinese J Org Chem 34:2236–2248

    Article  CAS  Google Scholar 

  3. Madhu S, Kalaiyarasi R, Basu SK, Jadhavb S, Ravikanth M (2014) A boron-dipyrrin–mercury (II) complex as a fluorescence turn-on sensor for chloride and applications towards logic gates. J Mater Chem C 2:2534–2544

    Article  CAS  Google Scholar 

  4. Liu J, He XX, Zhang J, He T, Huang LQ, Shen JQ, Li D, Qiu HY, Yin SC (2015) A BODIPY derivative for colorimetric and fluorometric sensing of fluoride ion and its logic gates behavior. Sensors Actuators B Chem 208:538–545

    Article  CAS  Google Scholar 

  5. Gareis T, Huber C, Wolfbeis OS, Daub J (1997) Phenol/phenolate-dependent on/off switching of the luminescence of 4,4-difluoro-4-Bora-3a,4a-diaza-S-indacenes. Chem Commun 18:1717–1718

    Article  Google Scholar 

  6. Werner T, Huber C, Heinl S, Kollmannsberger M, Daub J, Wolfbeis OS (1997) Novel optical Ph-sensor based on a boradiaza-indacene derivative. Fresenius J Anal Chem 359:150–154

    Article  CAS  Google Scholar 

  7. Sui B, Tang S, Liu T (2014) Novel BODIPY-based fluorescence turn-on sensor for Fe3+ and its bioimaging application in living cells. ACS Appl Mater Interfaces 21:18408–18412

    Article  Google Scholar 

  8. Andrea B, Costero M, Salvador AG (2014) Chromo-fluorogenic BODIPY-complexes for selective detection of V-type nerve agent surrogates. Chem Commun 50:13289–13291

    Article  Google Scholar 

  9. Fengling S, Yingying X, Xu W, Jingyun W, Xiaoqing X, Xiaojun P (2014) Ratiometric fluorescent probe based on novel red-emission BODIPY for determination of bovine serum albumin. Chem Res Chin Univ 30:738–742

    Article  Google Scholar 

  10. Ma D, Kim D, Seo E, Lee S, Ahn KH (2015) Ratiometric fluorescence detection of cysteine and homocysteine with a BODIPY dye by mimicking the native chemical ligation. Analyst 140:422–427

    Article  CAS  PubMed  Google Scholar 

  11. Bahaidarah E, Harriman A, Stachelek P, Rihn S, Heyerb E, Ziessel R (2014) Fluorescent molecular rotors based on the BODIPY motif: effect of remote substituents. Photochem Photobiol Sci 10:1397–1401

    Article  Google Scholar 

  12. Marfin YS, Merkushev DA, Levshanov GA, Rumyantsev EV (2014) Fluorescent properties of 8-phenylBODIPY in ethanol – ethylene glycol mixed solutions. J Fluoresc 24:1613–1619

    Article  CAS  PubMed  Google Scholar 

  13. Rongrong H, Lager E, Aguilar-Aguilar A, Liu J, Lam JWY, Sung HHY, Williams ID (2009) Twisted intramolecular charge transfer and aggregation-induced emission of BODIPY derivatives. J Phys Chem C 113:15845–15853

    Article  Google Scholar 

  14. Dal Molin M, Verolet Q, Soleimanpour S, Matile S (2015) Mechanosensitive membrane probes. Chemistry 21:6012–6021

    Article  CAS  PubMed  Google Scholar 

  15. Haidekker M, Theodorakis E (2010) Environment-sensitive behavior of fluorescent molecular rotors. J Biol Eng 4:11–25

    Article  PubMed Central  PubMed  Google Scholar 

  16. Benniston AC (2014) Monitoring rheological properties in biological systems by fluorescence spectroscopy using borondipyrromethene (Bodipy) dyes: a mini review. J Anal Bioanal Tech 5:1–11

    Article  Google Scholar 

  17. Forster T, Hoffmann G (1971) Effect of viscosity on the fluorescence quantum yield of some dye systems. Z Phys Chem 75:63–76 (in German)

    Article  Google Scholar 

  18. Weissberger A, Proskauer ES, Riddick JA, Toops EE (1955) Organic solvents. Physical properties and methods of purification. Interscience Publishers Inc, New York

    Google Scholar 

  19. Bruttel P, Schlink R (2003) Water determination by Karl Fischer titration. Metrohm Monogr 8(5003):2003–2009.

  20. Wolfbeis OS (2008) Standardization and quality assurance in fluorescence measurements techniques. Springer Ser Fluoresc. doi:10.1007/978-3-540-75207-3

    Google Scholar 

  21. Marfin YS, Rumyantsev EV, Ya SF, Antina EV (2012) Relationship between the spectral properties of solutions of borofluoride complex of alkylated dipyrromethene and the physicochemical parameters of solvents. Russ J Phys Chem A 86:1068–1072

    Article  CAS  Google Scholar 

  22. Arbeloa TL (1999) Correlations between photophysics and lasing properties of dipyrromethene–bf2 dyes in solution. Chem Phys Lett 299:315–321

    Article  CAS  Google Scholar 

  23. Volchkov VV, Khimich MN, Ya MM, Uzhinov BM (2013) A fluorescence study of the excited-state dynamics of boron dipyrrin molecular rotors. High Energy Chem 47:224–229

    Article  CAS  Google Scholar 

  24. Jeyanthy S, Lichlyter D, Wright NE, Dakanali M, Haidekker M, Theodorakis E (2010) Molecular rotors: synthesis and evaluation as viscosity sensors. Tetrahedron 66:2582–2588

    Article  Google Scholar 

  25. Giulio M, Martinelli E, Ruggeri G, Galli G, Pucci A (2015) Julolidine fluorescent molecular rotors as vapour sensing probes in polystyrene films. Dye Pigment 113:47–54

    Article  Google Scholar 

  26. Ling KH, Kirmaier C, Yu L, Thamyongkit P, Youngblood WJ, Calder ME, Ramos L et al (2005) Structural control of the photodynamics of boron - dipyrrin complexes. J Phys Chem B 109:20433–20443

    Article  Google Scholar 

  27. Gordon H, Ruseckas A, Harriman A, Samuel IDW (2011) Conformational effects on the dynamics of internal conversion in boron dipyrromethene dyes in solution. Angew Chem Int Ed 50:6634–6637

    Article  Google Scholar 

  28. Rezende LC, Vaidergorn M, Moraes JCB, da Silva Emery F (2014) Synthesis, photophysical properties and solvatochromism of meso-substituted tetramethyl BODIPY dyes. J Fluoresc 24:257–266

    Article  Google Scholar 

  29. Banuelos J, Lopez Arbeloa F, Arbeloa T, Salleres S, Vilas JL, Amat-Guerri F, Liras M, Lopez Arbeloa I (2008) Photophysical characterization of new 3-amino and 3-acetamido BODIPY dyes with solvent sensitive properties. J Fluoresc 18:899–907

    Article  CAS  PubMed  Google Scholar 

  30. Lager E, Liu J, Aguilar-Aguilar A, Zhong Tang B, Pena-Cabrera E (2009) Novel meso-polyarylamine-BODIPY hybrids: synthesis and study of their optical properties. J Org Chem 74:2053–2058

    Article  CAS  PubMed  Google Scholar 

  31. Banuelos PJ, Lopez Arbeloa F, Martinez Martinez V, Lopez Arbeloa T, Lopez Arbeloa I (2004) Photophysical properties of the pyrromethene 597 dye: solvent effect. J Phys Chem A 108:5503–5508

    Article  Google Scholar 

  32. Marfin YS, Rumyantsev EV (2014) Analysis of solvation and structural contributions in spectral characteristics of dipyrrin Zn(II) complexes. Spectrochim Acta A Mol Biomol Spectrosc 130:423–428

    Article  CAS  PubMed  Google Scholar 

  33. Chaudhuri T (2010) Photophysical properties of the 8-phenyl analogue of PM567: a theoretical rationalization. Spectrochim Acta A Mol Biomol Spectrosc 75:739–744

    Article  PubMed  Google Scholar 

  34. Alamiry MAH, Benniston AC, Copley G, Elliott KJ, Harriman A, Stewart B, Zhi YG (2008) A molecular rotor based on an unhindered boron dipyrromethene (Bodipy) dye. Chem Mater 20:4024–4032

    Article  CAS  Google Scholar 

  35. Krestov GA, Afanas’yev VN, Yefremova LS (1988) Physical and chemical properties of binary solvents: handbook. Khimiya, Leningrad, p 688. (in Russian)

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Acknowledgments

The work was supported by the grants of the Russian Foundation for Basic Research (No 14-03-31888, No 15-33-20002) and the grant of the President of the Russian Federation for young scientists and graduate students engaged in advanced research and development in priority directions of modernization of the Russian economics (2013 – 2015) (Grant No. SP-1742.2013.1).

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  1. Department of Inorganic Chemistry, Ivanovo State University of Chemistry and Technology, 7 Sheremetevsky str, 153000, Ivanovo, Russia

    Yuriy S. Marfin, Dmitry A. Merkushev, Sergey D. Usoltsev, Maria V. Shipalova & Evgeniy V. Rumyantsev

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  1. Yuriy S. Marfin
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  2. Dmitry A. Merkushev
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  3. Sergey D. Usoltsev
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  5. Evgeniy V. Rumyantsev
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Correspondence to Yuriy S. Marfin.

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Marfin, Y.S., Merkushev, D.A., Usoltsev, S.D. et al. Fluorescent Properties of 8-Substituted BODIPY Dyes: Influence of Solvent Effects. J Fluoresc 25, 1517–1526 (2015). https://doi.org/10.1007/s10895-015-1643-9

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  • DOI: https://doi.org/10.1007/s10895-015-1643-9

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