skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures

Authors:
; ; ; ; ; ; ; ; ; ; ; ; ; ;
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Photosynthetic Antenna Research Center (PARC)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1384899
DOE Contract Number:  
SC0001035
Resource Type:
Journal Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 4; Journal Issue: 5; 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 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
solar (fuels), photosynthesis (natural and artificial), biofuels (including algae and biomass), bio-inspired, charge transport, membrane, synthesis (novel materials), synthesis (self-assembly)

Citation Formats

Reddy, Kanumuri Ramesh, Jiang, Jianbing, Krayer, Michael, Harris, Michelle A., Springer, Joseph W., Yang, Eunkyung, Jiao, Jieying, Niedzwiedzki, Dariusz M., Pandithavidana, Dinesh, Parkes-Loach, Pamela S., Kirmaier, Christine, Loach, Paul A., Bocian, David F., Holten, Dewey, and Lindsey, Jonathan S. Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures. United States: N. p., 2013. Web. doi:10.1039/C3SC22317E.
Reddy, Kanumuri Ramesh, Jiang, Jianbing, Krayer, Michael, Harris, Michelle A., Springer, Joseph W., Yang, Eunkyung, Jiao, Jieying, Niedzwiedzki, Dariusz M., Pandithavidana, Dinesh, Parkes-Loach, Pamela S., Kirmaier, Christine, Loach, Paul A., Bocian, David F., Holten, Dewey, & Lindsey, Jonathan S. Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures. United States. doi:10.1039/C3SC22317E.
Reddy, Kanumuri Ramesh, Jiang, Jianbing, Krayer, Michael, Harris, Michelle A., Springer, Joseph W., Yang, Eunkyung, Jiao, Jieying, Niedzwiedzki, Dariusz M., Pandithavidana, Dinesh, Parkes-Loach, Pamela S., Kirmaier, Christine, Loach, Paul A., Bocian, David F., Holten, Dewey, and Lindsey, Jonathan S. Tue . "Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures". United States. doi:10.1039/C3SC22317E.
@article{osti_1384899,
title = {Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures},
author = {Reddy, Kanumuri Ramesh and Jiang, Jianbing and Krayer, Michael and Harris, Michelle A. and Springer, Joseph W. and Yang, Eunkyung and Jiao, Jieying and Niedzwiedzki, Dariusz M. and Pandithavidana, Dinesh and Parkes-Loach, Pamela S. and Kirmaier, Christine and Loach, Paul A. and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.},
abstractNote = {},
doi = {10.1039/C3SC22317E},
journal = {Chemical Science},
issn = {2041-6520},
number = 5,
volume = 4,
place = {United States},
year = {2013},
month = {1}
}

Works referenced in this record:

Swallowtail Bacteriochlorins. Lipophilic Absorbers for the Near-Infrared
journal, May 2008

  • Borbas, K. Eszter; Lindsey, Jonathan S.
  • Organic Letters, Vol. 10, Issue 10
  • DOI: 10.1021/ol800436u

Investigation of MALDI-TOF Mass Spectrometry of Diverse Synthetic Metalloporphyrins, Phthalocyanines and Multiporphyrin Arrays
journal, April 1999


Crystal Structure of the RC-LH1 Core Complex from Rhodopseudomonas palustris
journal, December 2003


Structural characteristics that make chlorophylls green: interplay of hydrocarbon skeleton and substituents
journal, January 2011

  • Mass, Olga; Taniguchi, Masahiko; Ptaszek, Marcin
  • New J. Chem., Vol. 35, Issue 1
  • DOI: 10.1039/C0NJ00652A

Biodistribution and Photodynamic Efficacy of a Water-Soluble, Stable, Halogenated Bacteriochlorin against Melanoma
journal, January 2011

  • Dąbrowski, Janusz M.; Urbanska, Krystyna; Arnaut, Luis G.
  • ChemMedChem, Vol. 6, Issue 3
  • DOI: 10.1002/cmdc.201000524

Photophysical Properties and Electronic Structure of Stable, Tunable Synthetic Bacteriochlorins: Extending the Features of Native Photosynthetic Pigments
journal, September 2011

  • Yang, Eunkyung; Kirmaier, Christine; Krayer, Michael
  • The Journal of Physical Chemistry B, Vol. 115, Issue 37
  • DOI: 10.1021/jp205258s

De novo synthesis and photophysical characterization of annulated bacteriochlorins. Mimicking and extending the properties of bacteriochlorophylls
journal, January 2011

  • Krayer, Michael; Yang, Eunkyung; Diers, James R.
  • New Journal of Chemistry, Vol. 35, Issue 3, p. 587-601
  • DOI: 10.1039/c0nj00771d

The solution structure of Rhodobacter sphaeroides LH1β reveals two helical domains separated by a more flexible region: structural consequences for the LH1 complex
journal, April 2000

  • Conroy, Matthew J.; Westerhuis, Willem H. J.; Parkes-Loach, Pamela S.
  • Journal of Molecular Biology, Vol. 298, Issue 1
  • DOI: 10.1006/jmbi.2000.3649

High-yielding syntheses of hydrophilic conjugatable chlorins and bacteriochlorins
journal, January 2009

  • McCarthy, Jason R.; Bhaumik, Jayeeta; Merbouh, Nabyl
  • Organic & Biomolecular Chemistry, Vol. 7, Issue 17
  • DOI: 10.1039/b908713c

Galactosyl Human Serum Albumin-NMP1 Conjugate: A Near Infrared (NIR)-Activatable Fluorescence Imaging Agent to Detect Peritoneal Ovarian Cancer Metastases
journal, July 2012

  • Alexander, Vinita M.; Sano, Kohei; Yu, Zhanqian
  • Bioconjugate Chemistry, Vol. 23, Issue 8
  • DOI: 10.1021/bc3002419

Tapping the near-infrared spectral region with bacteriochlorin arrays
journal, January 2011

  • Lindsey, Jonathan S.; Mass, Olga; Chen, Chih-Yuan
  • New Journal of Chemistry, Vol. 35, Issue 3
  • DOI: 10.1039/c0nj00977f

De Novo Synthesis of Stable Tetrahydroporphyrinic Macrocycles:  Bacteriochlorins and a Tetradehydrocorrin
journal, July 2005

  • Kim, Han-Je; Lindsey, Jonathan S.
  • The Journal of Organic Chemistry, Vol. 70, Issue 14
  • DOI: 10.1021/jo050467y

Regioselective 15-Bromination and Functionalization of a Stable Synthetic Bacteriochlorin
journal, July 2007

  • Fan, Dazhong; Taniguchi, Masahiko; Lindsey, Jonathan S.
  • The Journal of Organic Chemistry, Vol. 72, Issue 14
  • DOI: 10.1021/jo070785s

Energy-transfer dynamics in three light-harvesting mutants of Rhodobacter sphaeroides: a picosecond spectroscopy study
journal, April 1990

  • Hunter, C. Neil; Bergstroem, Hans; Van Grondelle, Rienk
  • Biochemistry, Vol. 29, Issue 13
  • DOI: 10.1021/bi00465a008

Multifunctional Bacteriochlorins from Selective Palladium-Coupling Reactions
journal, July 2012

  • Yu, Zhanqian; Ptaszek, Marcin
  • Organic Letters, Vol. 14, Issue 14
  • DOI: 10.1021/ol3015545

The crystal structure of the light-harvesting complex II (B800–850) from Rhodospirillum molischianum
journal, May 1996


1,3-Dipolar Cycloaddition Reactions of Porphyrins with Azomethine Ylides
journal, March 2005

  • Silva, Ana M. G.; Tomé,, Augusto C.; Neves, Maria G. P. M. S.
  • The Journal of Organic Chemistry, Vol. 70, Issue 6
  • DOI: 10.1021/jo048349i

Porphyrins
journal, January 1969


Discrete Cyclic Porphyrin Arrays as Artificial Light-Harvesting Antenna
journal, December 2009

  • Aratani, Naoki; Kim, Dongho; Osuka, Atsuhiro
  • Accounts of Chemical Research, Vol. 42, Issue 12
  • DOI: 10.1021/ar9001697

Expanded Bacteriochlorins
journal, April 2012

  • Samankumara, Lalith P.; Wells, Sarah; Zeller, Matthias
  • Angewandte Chemie International Edition, Vol. 51, Issue 23
  • DOI: 10.1002/anie.201201124

Synthesis, Photophysical and Electrochemistry of Near-IR Absorbing Bacteriochlorins Related to Bacteriochlorophyll a
journal, October 2012

  • Kozyrev, Andrei; Ethirajan, Manivannan; Chen, Ping
  • The Journal of Organic Chemistry, Vol. 77, Issue 22
  • DOI: 10.1021/jo301895p

In Vitro Self-Assembly of the Light Harvesting Pigment-Protein LH2 Revealed by Ultrafast Spectroscopy and Electron Microscopy
journal, April 2004


Photoprotection in a purple phototrophic bacterium mediated by oxygen-dependent alteration of carotenoid excited-state properties
journal, May 2012

  • Slouf, V.; Chabera, P.; Olsen, J. D.
  • Proceedings of the National Academy of Sciences, Vol. 109, Issue 22
  • DOI: 10.1073/pnas.1201413109

Structure of the Rhodobacter sphaeroides Light-Harvesting 1 β Subunit in Detergent Micelles ,
journal, January 2002

  • Sorgen, Paul L.; Cahill, Sean M.; Krueger-Koplin, Ray D.
  • Biochemistry, Vol. 41, Issue 1
  • DOI: 10.1021/bi011576j

Porphyrins and other pyrrolic macrocycles in cycloaddition reactions
journal, April 2009

  • Tomé, Augusto C.; Neves, Maria G. P. M. S.; Cavaleiro, José A. S.
  • Journal of Porphyrins and Phthalocyanines, Vol. 13, Issue 04n05
  • DOI: 10.1142/S1088424609000619

A trans-AB-Bacteriochlorin Building Block
journal, November 2011

  • Mass, Olga; Lindsey, Jonathan S.
  • The Journal of Organic Chemistry, Vol. 76, Issue 22, p. 9478-9487
  • DOI: 10.1021/jo201967k

Synthesis and Photophysical Properties of Thioglycosylated Chlorins, Isobacteriochlorins, and Bacteriochlorins for Bioimaging and Diagnostics
journal, November 2010

  • Singh, Sunaina; Aggarwal, Amit; Thompson, Sebastian
  • Bioconjugate Chemistry, Vol. 21, Issue 11
  • DOI: 10.1021/bc100356z

Fast and Robust Route to Hydroporphyrin−Chalcones with Extended Red or Near-Infrared Absorption
journal, April 2009

  • Ruzié, Christian; Krayer, Michael; Lindsey, Jonathan S.
  • Organic Letters, Vol. 11, Issue 8
  • DOI: 10.1021/ol900277m


journal, August 2008

  • Grin, Mikhail; Mironov, Andrey; Shtil, Alexander
  • Anti-Cancer Agents in Medicinal Chemistry, Vol. 8, Issue 6
  • DOI: 10.2174/187152008785133128

Accessing the near-infrared spectral region with stable, synthetic, wavelength-tunable bacteriochlorins
journal, January 2008

  • Taniguchi, Masahiko; Cramer, David L.; Bhise, Anil D.
  • New Journal of Chemistry, Vol. 32, Issue 6
  • DOI: 10.1039/b717803d


journal, October 2007


Energetics of Photophysical Processes in Chlorophyll-Like Molecules
journal, June 1970


[8π+2π] Cycloaddition of meso-Tetra- and 5,15-Diarylporphyrins: Synthesis and Photophysical Characterization of Stable Chlorins and Bacteriochlorins
journal, June 2011

  • Pereira, Nelson A. M.; Fonseca, Sofia M.; Serra, Arménio C.
  • European Journal of Organic Chemistry, Vol. 2011, Issue 20-21
  • DOI: 10.1002/ejoc.201100465

Biohybrid Photosynthetic Antenna Complexes for Enhanced Light-Harvesting
journal, February 2012

  • Springer, Joseph W.; Parkes-Loach, Pamela S.; Reddy, Kanumuri Ramesh
  • Journal of the American Chemical Society, Vol. 134, Issue 10
  • DOI: 10.1021/ja207390y

Determination of the absolute quantum yield of fluorescent solutions
journal, January 1957


Zinc-Bacteriochlorophyllide Dimers in de Novo Designed Four-Helix Bundle Proteins. A Model System for Natural Light Energy Harvesting and Dissipation
journal, June 2011

  • Cohen-Ofri, Ilit; van Gastel, Maurice; Grzyb, Joanna
  • Journal of the American Chemical Society, Vol. 133, Issue 24
  • DOI: 10.1021/ja202054m

Porphyrin, Chlorin, and Bacteriochlorin Isothiocyanates:  Useful Reagents for the Synthesis of Photoactive Bioconjugates
journal, March 2002

  • Sutton, J. M.; Clarke, O. J.; Fernandez, N.
  • Bioconjugate Chemistry, Vol. 13, Issue 2
  • DOI: 10.1021/bc015547x

Tailoring a Bacteriochlorin Building Block with Cationic, Amphipathic, or Lipophilic Substituents
journal, August 2008

  • Ruzié, Christian; Krayer, Michael; Balasubramanian, Thiagarajan
  • The Journal of Organic Chemistry, Vol. 73, Issue 15
  • DOI: 10.1021/jo800736c

Functionalized diphenylchlorins and bacteriochlorins: their synthesis and bioconjugation for targeted photodynamic therapy and tumour cell imaging
journal, November 2000


Comparison of the fluorescence kinetics of detergent-solubilized and membrane-reconstituted LH2 complexes from Rps. acidophila and Rb. sphaeroides
journal, October 2007

  • Pflock, Tobias; Dezi, Manuela; Venturoli, Giovanni
  • Photosynthesis Research, Vol. 95, Issue 2-3
  • DOI: 10.1007/s11120-007-9245-2


journal, August 2004


Theoretical Solar-to-Electrical Energy-Conversion Efficiencies of Perylene−Porphyrin Light-Harvesting Arrays
journal, December 2006

  • Hasselman, Georg M.; Watson, David F.; Stromberg, Jonathan R.
  • The Journal of Physical Chemistry B, Vol. 110, Issue 50
  • DOI: 10.1021/jp064547x

EFFECTS OF SOLVENT ON THE FLUORESCENCE PROPERTIES OF BACTERIOCHLOROPHYLL a
journal, November 1982


Expanded Scope of Synthetic Bacteriochlorins via Improved Acid Catalysis Conditions and Diverse Dihydrodipyrrin-Acetals
journal, February 2010

  • Krayer, Michael; Ptaszek, Marcin; Kim, Han-Je
  • The Journal of Organic Chemistry, Vol. 75, Issue 4, p. 1016-1039
  • DOI: 10.1021/jo9025572

Fluorescence quantum yields, lifetimes, and critical distances for energy transfer for chlorophyll ? and its pheophytin in solutions
journal, August 1986

  • Losev, A. P.; Sagun, E. I.; Kochubeev, G. A.
  • Journal of Applied Spectroscopy, Vol. 45, Issue 2
  • DOI: 10.1007/BF00657460

The absolute size of a photosynthetic unit
journal, May 1989

  • Mauzerall, David; Greenbaum, Nancy L.
  • Biochimica et Biophysica Acta (BBA) - Bioenergetics, Vol. 974, Issue 2
  • DOI: 10.1016/S0005-2728(89)80365-2

Synthesis and Physicochemical Properties of Metallobacteriochlorins
journal, August 2012

  • Chen, Chih-Yuan; Sun, Erjun; Fan, Dazhong
  • Inorganic Chemistry, Vol. 51, Issue 17
  • DOI: 10.1021/ic301262k