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Introduction of various substitutions to the methine bridge of heptamethine cyanine dyes Via substituted dianil linkers

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Abstract

The unique optical properties of cyanine dyes have prompted their use in numerous applications. Heptamethine cyanines are commonly modified on the methine bridge after synthesis of a meso-chlorine containing cyanine. Herein, a series of heptamethine cyanines containing modified methine bridges were synthesized using substituted dianil linkers. Their optical properties including, molar absorptivity, fluorescence, and quantum yield were measured as well as their hydrophobic effects in polar buffer solution. It was shown that dyes containing cyclopentene in the methine bridge or a phenyl ring in the meso position display increased molar absorptivity while the increased flexibility of the dye containing a cycloheptene in the methine bridge prevented fluorescence.

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Acknowledgments

The authors would like to thank the Department of Chemistry at Georgia State University for the support of the Ph.D. dissertation of AL and the MSc. thesis of FM. This study was supported by grants to MH from the Georgia State University Brains and Behavior Seed Grant, the Atlanta Clinical and Translational Science Institute Healthcare Innovation Seed Grant, and the Georgia Research Alliance Ventures Phase 1 Grant. MH would like thank the U.S. Department of Health and Human Services, National Institutes of Health National Institute of Biomedical Imaging and Bioengineering (Grant Number: RO1EB022230).

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Authors and Affiliations

  1. Department of Chemistry, Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA, 30303, USA

    Andrew Levitz, Fahad Marmarchi & Maged Henary

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  1. Andrew Levitz
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  2. Fahad Marmarchi
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  3. Maged Henary
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Correspondence to Maged Henary.

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Levitz, A., Marmarchi, F. & Henary, M. Introduction of various substitutions to the methine bridge of heptamethine cyanine dyes Via substituted dianil linkers. Photochem Photobiol Sci 17, 1409–1416 (2018). https://doi.org/10.1039/c8pp00218e

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  • DOI: https://doi.org/10.1039/c8pp00218e

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