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.
Highlights
Nature’s “advanced functional dyes”—chosen by the fine comb of evolution [1,2,3,4,5,6]—are the chlorophylls and their analogues
We previously prepared a set of chlorins containing PEG groups for water-solubilization (Figure 3)
Chlorins I and II each contain three PEG groups, which were installed by click chemistry with a
Summary
Nature’s “advanced functional dyes”—chosen by the fine comb of evolution [1,2,3,4,5,6]—are the chlorophylls and their analogues. The structures of chlorophyll a and chlorophyll b are shown in Figure 1 [7]. Chlorophylls a and b absorb strongly in the blue (and near-ultraviolet) and in the red spectral regions; green light is absorbed with weaker intensity, the characteristic color of the compounds in thin films (e.g., a leaf) or dilute solutions, and the verdant landscapes of Earth [8,9]. 130 the characteristic color of the compounds in thin films (e.g., a leaf) or dilute solutions, and of 30 intensity, the verdant landscapes of Earth [8,9]. A longstanding objective in photochemistry, artificial photosynthesis and allied disciplines has been to create synthetic chlorophyll-like molecules as a means to examine the structural has
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