Abstract
Fluorescent characteristics of two BODIPY dyes in solutions were investigated under the viscosity variations. Investigated dyes differ in the nature of 8-substituent of ligand molecule. Viscosity variation was achieved by changing of solvent composition in the binary system ethanol - ethylene glycol and solvent temperature. 8-Phenyl substituted BODIPY is found to exhibit properties of molecular rotor, i.e. its fluorescent characteristics are highly dependent on the viscosity or rigidity of the microenvironment. Increased temperature leads to a linear decrease of fluorescence parameters unlike the solvent composition variation where fluorescence change is nonlinear. The highest specific change in the fluorescence was observed in pure ethanol. Change in the nonradiative decay rate constant values with the increasing of viscosity indicates that the analyzed phenyl substituted complex is a true molecular rotor. Investigated 8-phenylBODIPY could be recommended as promising viscosity sensor in different organic media.
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References
Kottas GS, Clarke LI, Horinek D, Michl J (2005) Artificial molecular rotors. Chem Rev 105:1281–1376
Grabowski ZR, Rotkiewicz K, Rettig W (2003) Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures. Chem Rev 103:3899–4032
Dragan A, Graham AE, Geddes CD (2014) Fluorescence-based broad dynamic range viscosity probes. J Fluoresc 24:397–402
Haidekker MA, Theodorakis EA (2007) Molecular rotors—fluorescent biosensors for viscosity and flow. Org Biomol Chem 5:1669–1678
Geddes CD, Chevers JM, Birch DJ (1999) Probing the sol–gel transition in SiO2 hydrogels – a new application of near-infrared fluorescence. J Fluoresc 9(1):73–79
Geddes CD (2002) 1- and 2-photon fluorescence anisotropy decay to probe the kinetic and structural evolution of sol–gel glasses: a summary. J Fluoresc 12(3–4):343–367
Antina EV, Rumyantsev EV (2009) The Chemistry of bilirubin and its analogies. Krasand, Moscow (in Russian)
Nierth A, Kobitski AY, Nienhaus GU, Jaschke A (2010) Anthracene − BODIPY dyads as fluorescent sensors for biocatalytic diels − alder reactions. J Am Chem Soc 132:2646–2654
Banuelos J, Arbeloa FL, Arbeloa T, Salleres S, Vilas JL, Amat-Guerri F, Liras M, Arbeloa IL (2008) Photophysical Characterization of new 3-amino and 3-acetamido BODIPY dyes with solvent sensitive properties. J Fluoresc 18(5):899–907
Marfin YS, Rumyantsev EV, Fadeev YS, 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(7):1068–1072
Quan L, Sun T, Lin W, Guan X, Zheng M, Xie Z, Jing X (2014) BODIPY fluorescent chemosensor for Cu2+ detection and its applications in living cells: fast response and high sensitivity. J Fluoresc 24(3):841–846
Spangenburg EE, Pratt SJ, Wohlers LM, Lovering RM (2011) Use of BODIPY (493/503) to visualize intramuscular lipid droplets in skeletal muscle. J Biomed Biotechnol. doi:10.1155/2011/598358
Boldyrev IA, Zhai X, Momsen MM, Brockman HL, Brown RE, Molotkovsky JG (2007) New BODIPY lipid probes for fluorescence studies of membranes. J Lipid Res 48(7):1518–1532
Kamkaew A, Lim SH, Lee HB, Kiew LV, Chung LY, Burgess K (2013) BODIPY dyes in photodynamic therapy. Chem Soc Rev 42(1):77–88
Lopez Arbeloa F, Banuelos J, Martinez V, Arbeloa T, Lopez Arbeloa I (2005) Structural, photophysical and lasing properties of pyrromethene dyes. Int Rev Phys Chem 24:339–374
Burghart A, Kim H, Welch MB, Thoresen LH, Reibenspies J (1999) 3,5-diaryl-4,4-difluoro-4-Bora-3a,4a-diaza-s-indacene (BODIPY) dyes: synthesis, spectroscopic, electrochemical, and structural properties. J Org Chem 64:7813–7819
Kim B, Ma B, Donuru VR, Liuc H, Frechet JMJ (2010) BODIPY-backboned polymers as electron donor in bulk heterojunction solar cells. Chem Commun 46:4148–4150
Kuimova MK, Yahioglu G, Levitt JA, Suhling K (2008) Molecular rotor measures viscosity of live cells via fluorescence lifetime imaging. J Am Chem Soc 130:6672–6673
Volchkov VV, Khimich MN, Mel’nikov MY, Uzhinov BM (2013) A Fluorescence study of the excited-state dynamics of boron dipyrrin molecular rotors. High Energy Chem 47(5):226–231
Yin X, Li Y, Zhu Y, Jing X, Li Y, Zhu D (2010) A highly sensitive viscosity probe based on ferrocene-BODIPY dyads. Dalton Trans 39:9929–9935
Sunahara H, Urano Y, Kojima H, Nagano T (2007) Design and synthesis of a library of BODIPY-based environmental polarity sensors utilizing photoinduced electron transfer-controlled fluorescence ON/OFF switching. J Am Chem Soc 129:5597–5604
Li F, Yang SI, Ciringh Y, Seth J, Martin CH et al (1998) Design, synthesis, and photodynamics of light-harvesting arrays comprised of a porphyrin and one, two, or eight boron-dipyrrin accessory pigments. J Am Chem Soc 120:10001–10017
Kee HL, Kirmaier C, Yu L, Thamyongkit P (2005) Structural control of the photodynamics of boron-dipyrrin complexes. J Phys Chem B 109:20433–20443
Hedley GJ, 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
Rumyantsev EV, Marfin YS, Antina EV (2010) Donor-acceptor complexes of dipyrrolylmethenes with boron trifluoride as intermediates in the synthesis of BODIPY. Russ Chem Bull 59:1890–1895
Rumyantsev EV, Alyoshin SN, Marfin YS (2013) Kinetic study of BODIPY resistance to acids and alkalis: stability ranges in aqueous and non-aqueous solutions. Inorg Chim Acta 408:181–185
Weissberger A, Proskauer ES, Riddick JA, Toops EE Jr (1955) Organic solvents. Physical properties and methods of purification. Interscience Publishers Inc, New York
Bruttel P, Schlink R (2003) Water determination by Karl Fischer Titration. Monograph, Metrohm
Wolfbeis OS (2008) Springer series on fluorescence. standardization and quality assurance in fluorescence measurements techniques. DOI 10.1007/978-3-540-75207-3
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)
Balankina ES, Lyashenko AK (2003) The packing coefficient and volumetric-elastic properties of solutions. J Mol Liq 103:211–220
Yin X, Li Y, Zhu Y, Jing X, Li Y, Zhu D (2010) A highly sensitive viscosity probe based on ferrocene-BODIPY dyads. Dalton Trans 39:9929–9935
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
Acknowledgments
The work was supported by the grant of the Russian Foundation for Basic Research (Grant No 14-03-31888) 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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Marfin, Y.S., Merkushev, D.A., Levshanov, G.A. et al. Fluorescent Properties of 8-phenylBODIPY in Ethanol – Ethylene Glycol Mixed Solutions. J Fluoresc 24, 1613–1619 (2014). https://doi.org/10.1007/s10895-014-1447-3
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DOI: https://doi.org/10.1007/s10895-014-1447-3