U.S. Department of EnergyOffice of Scientific and Technical Information
Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media
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.
- Authors:
-
[1]
- North Carolina State Univ., Raleigh, NC (United States)
- Washington Univ., St. Louis, MO (United States)
- NIRvana Sciences, Inc., Research Triangle Park, NC (United States)
- Publication Date:
- Research Org.:
- Energy Frontier Research Centers (EFRC) (United States). Photosynthetic Antenna Research Center (PARC); Washington Univ., St. Louis, MO (United States); Energy Frontier Research Centers (EFRC) (United States). Energy Frontier Research Center for Inorganometallic Catalyst Design (ICDC)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1470069
- Alternate Identifier(s):
- OSTI ID: 1511007
- Grant/Contract Number:
- SC0001035; SC0012702
- Resource Type:
- Journal Article: Accepted Manuscript
- Journal Name:
- Molecules
- Additional Journal Information:
- Journal Volume: 23; Journal Issue: 1; Related Information: PARC partners with Washington University in St. Louis (lead); University of California, Riverside; University of Glasgow, UK; Los Alamos National Laboratory; University of New Mexico; New Mexico Corsortium; North Carolina State University; Northwestern University; Oak Ridge National Laboratory; University of Pennsylvania; Sandia National Laboratories; University of Sheffield, UK; Journal ID: ISSN 1420-3049
- Publisher:
- MDPI
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 59 BASIC BIOLOGICAL SCIENCES; amphiphilic; bioconjugation; chlorin; fluorescence; micelle; Poisson; PEG; protein
Citation Formats
Liu, Rui, Liu, Mengran, Hood, Don, Chen, Chih-Yuan, MacNevin, Christopher, Holten, Dewey, and Lindsey, Jonathan. Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media. United States: N. p., 2018.
Web. doi:10.3390/molecules23010130.
Liu, Rui, Liu, Mengran, Hood, Don, Chen, Chih-Yuan, MacNevin, Christopher, Holten, Dewey, & Lindsey, Jonathan. Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media. United States. https://doi.org/10.3390/molecules23010130
Liu, Rui, Liu, Mengran, Hood, Don, Chen, Chih-Yuan, MacNevin, Christopher, Holten, Dewey, and Lindsey, Jonathan. 2018.
"Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media". United States. https://doi.org/10.3390/molecules23010130. https://www.osti.gov/servlets/purl/1470069.
@article{osti_1470069,
title = {Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media},
author = {Liu, Rui and Liu, Mengran and Hood, Don and Chen, Chih-Yuan and MacNevin, Christopher and Holten, Dewey and Lindsey, Jonathan},
abstractNote = {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.},
doi = {10.3390/molecules23010130},
url = {https://www.osti.gov/biblio/1470069},
journal = {Molecules},
issn = {1420-3049},
number = 1,
volume = 23,
place = {United States},
year = {Wed Jan 10 00:00:00 EST 2018},
month = {Wed Jan 10 00:00:00 EST 2018}
}
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Two Complementary Routes to 7-Substituted Chlorins. Partial Mimics of Chlorophyll b
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Salt Effects on Solute Exchange in Sodium Dodecyl Sulfate Micelles
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Synthesis of Ethyne-Linked or Butadiyne-Linked Porphyrin Arrays Using Mild, Copper-Free, Pd-Mediated Coupling Reactions
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