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Molecules 2018, 23(1), 130; doi:10.3390/molecules23010130

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

1
Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA
2
Department of Chemistry, Washington University, St. Louis, MO 63130-4889, USA
3
NIRvana Sciences, Inc., Research Triangle Park, NC 27709, USA
*
Authors to whom correspondence should be addressed.
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)
View Full-Text   |   Download PDF [8201 KB, uploaded 10 January 2018]   |  

Abstract

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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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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