Insights into bishemicyanines with long emission wavelengths and high sensitivity in viscous environments |
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| Affiliation: | 1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China;2. School of Chemical and Environmental Engineering, Liaoning University of Technology, Jinzhou 121001, China;1. St. Petersburg State University, Biology Department, Universitetskaya Nab. 7-9, 199034, St. Petersburg, Russia;2. St. Petersburg State University, Institute of Chemistry, St. Petersburg, Universitetskii Pr. 26, 198504, Russia;3. Institute of Macromolecular Compounds, Russian Academy of Sciences, Bolshoi Pr. V.O., 31, 199004, St. Petersburg, Russia;4. St. Petersburg State University, Department of Physics, Ulianovskaya St. 3, 198504, St. Petersburg, Russia;5. Research Institute of Nanobiotechnologies, St. Petersburg State Polytechnical University, Polytechnicheskaya St. 29, 195251, St. Petersburg, Russia;6. Russian Research Center for Radiology and Surgical Technologies, Leningradskaya St. 70, 197758, St. Petersburg, Russia;7. Becker & Hickl GmbH, Nahmitzer Damm 30, 12277, Berlin, Germany;8. Department of Biomathematics, Institute of Physiology of the Czech Academy of Sciences, Videnska 1083, 14220 Prague 4, Czech Republic;9. Department of Chemistry, University of Eastern Finland, 80101, Joensuu, Finland;1. College of Chemistry and Molecular Sciences, Key Laboratory of Biomedical Polymers of Ministry of Education, Wuhan University, Wuhan 430072, China;2. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China;1. Department of Chemistry, Indian Institute of Technology Gandhinagar, Palaj, Gandhinagar, 382 355, India;2. Radiation & Photochemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai, 400 085, India;3. Homi Bhabha National Institute, Training School Complex, Anushaktinagar, Mumbai, 400 094, India;4. Department of Biological Engineering, Indian Institute of Technology Gandhinagar, Palaj Gandhinagar, 382355, India |
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| Abstract: | A systematic spectral analysis was presented for bishemicyanine dyes (Hsd and D2) and monohemicyanine dyes (Hs and DSMI). The bishemicyanine dyes displayed long emission wavelengths, large Stokes shifts, low background quantum yields in aqueous solutions and high sensitivity in viscous environments. Better understanding of the structure-property relationships could benefit the design of improved dyes. Computational studies on these dyes revealed the three conjugated forms of bishemicyanines are in equilibrium due to two positive charges and a branched bulk substituent. Bishemicyanines possessed obviously lower rotating energy barrier of C C bond rotation compared to the monohemicyanine dyes. Moreover, the synergetic effects of the rotation about the ϕ4 bond, ϕ5 bond and ϕ7 bond of the bishemicyanines (Hsd and D2) lead to lower fluorescence quantum yields in a free state and larger fluorescence quantum yield enhancements in viscous environment compared to that of monohemicyanine dyes (Hs and DSMI). The results demonstrate a foundation for interpretation of the behavior of the dyes, thus providing guidelines for future of new bishemicyanine fluorophores with specific applications. |
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| Keywords: | Bishemicyanine dyes Long emission wavelength Low background quantum yield Rotating energy barrier Density functional calculations |
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