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Open AccessFeature PaperArticle

Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media

Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA
Department of Chemistry, Washington University, St. Louis, MO 63130-4889, USA
NIRvana Sciences, Inc., Research Triangle Park, NC 27709, USA
Authors to whom correspondence should be addressed.
Molecules 2018, 23(1), 130;
Received: 7 December 2017 / Revised: 4 January 2018 / Accepted: 6 January 2018 / Published: 10 January 2018
(This article belongs to the Special Issue Advanced Functional Dyes)
Fluorophores that absorb and emit in the red spectral region (600–700 nm) are of great interest in photochemistry and photomedicine. Eight new target chlorins (and 19 new chlorins altogether)—analogues of chlorophyll—of different polarities have been designed and synthesized for various applications; seven of the chlorins are equipped with a bioconjugatable tether. Hydrophobic or amphiphilic chlorins in a non-polar organic solvent (toluene), polar organic solvent (DMF), and aqueous or aqueous micellar media show a sharp emission band in the red region and modest fluorescence quantum yield (Φf = 0.2–0.3). A Poisson analysis implies most micelles are empty and few contain >1 chlorin. Water-soluble chlorins each bearing three PEG (oligoethyleneglycol) groups exhibit narrow emission bands (full-width-at-half maximum <25 nm). The lifetime of the lowest singlet excited state and the corresponding yields and rate constants for depopulation pathways (fluorescence, intersystem crossing, internal conversion) are generally little affected by the PEG groups or dissolution in aqueous or organic media. A set of chlorin–avidin conjugates revealed a 2-fold increase in Φf with increased average chlorin/avidin ratio (2.3–12). In summary, the chlorins of various polarities described herein are well suited as red-emitting fluorophores for applications in aqueous or organic media. View Full-Text
Keywords: amphiphilic; bioconjugation; chlorin; fluorescence; micelle; Poisson; PEG; protein amphiphilic; bioconjugation; chlorin; fluorescence; micelle; Poisson; PEG; protein
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MDPI and ACS Style

Liu, R.; Liu, M.; Hood, D.; Chen, C.-Y.; MacNevin, C.J.; Holten, D.; Lindsey, J.S. Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media. Molecules 2018, 23, 130.

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