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

Title: Hydrophilic tetracarboxy bacteriochlorins for photonics applications

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:
1384883
DOE Contract Number:  
SC0001035
Resource Type:
Journal Article
Journal Name:
Organic and Biomolecular Chemistry
Additional Journal Information:
Journal Volume: 12; 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 1477-0520
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

Jiang, Jianbing, Vairaprakash, Pothiappan, Reddy, Kanumuri Ramesh, Sahin, Tuba, Pavan, M. Phani, Lubian, Elisa, and Lindsey, Jonathan S. Hydrophilic tetracarboxy bacteriochlorins for photonics applications. United States: N. p., 2014. Web. doi:10.1039/C3OB41791C.
Jiang, Jianbing, Vairaprakash, Pothiappan, Reddy, Kanumuri Ramesh, Sahin, Tuba, Pavan, M. Phani, Lubian, Elisa, & Lindsey, Jonathan S. Hydrophilic tetracarboxy bacteriochlorins for photonics applications. United States. doi:10.1039/C3OB41791C.
Jiang, Jianbing, Vairaprakash, Pothiappan, Reddy, Kanumuri Ramesh, Sahin, Tuba, Pavan, M. Phani, Lubian, Elisa, and Lindsey, Jonathan S. Wed . "Hydrophilic tetracarboxy bacteriochlorins for photonics applications". United States. doi:10.1039/C3OB41791C.
@article{osti_1384883,
title = {Hydrophilic tetracarboxy bacteriochlorins for photonics applications},
author = {Jiang, Jianbing and Vairaprakash, Pothiappan and Reddy, Kanumuri Ramesh and Sahin, Tuba and Pavan, M. Phani and Lubian, Elisa and Lindsey, Jonathan S.},
abstractNote = {},
doi = {10.1039/C3OB41791C},
journal = {Organic and Biomolecular Chemistry},
issn = {1477-0520},
number = 1,
volume = 12,
place = {United States},
year = {2014},
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

Synthesis and evaluation of cationic bacteriochlorin amphiphiles with effective in vitro photodynamic activity against cancer cells at low nanomolar concentration
journal, January 2013

  • Sharma, Sulbha K.; Krayer, Michael; Sperandio, Felipe F.
  • Journal of Porphyrins and Phthalocyanines, Vol. 17, Issue 01n02
  • DOI: 10.1142/S108842461250126X

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


Palladium Porphyrin Containing Zirconium Phosphonate Langmuir−Blodgett Films
journal, April 1999

  • Nixon, Christine M.; Le Claire, Karine; Odobel, Fabrice
  • Chemistry of Materials, Vol. 11, Issue 4
  • DOI: 10.1021/cm980636d

Aggregation of equilibriums of xanthene dyes
journal, March 1972

  • Selwyn, Judith E.; Steinfeld, Jeffrey I.
  • The Journal of Physical Chemistry, Vol. 76, Issue 5
  • DOI: 10.1021/j100649a026

Synthesis of β-Galactose-Conjugated Chlorins Derived by Enyne Metathesis as Galectin-Specific Photosensitizers for Photodynamic Therapy
journal, December 2001

  • Zheng, Gang; Graham, Andrew; Shibata, Masayuki
  • The Journal of Organic Chemistry, Vol. 66, Issue 26
  • DOI: 10.1021/jo0105080

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

Synthetic bacteriochlorins with integral spiro-piperidine motifs
journal, January 2013

  • Reddy, Kanumuri Ramesh; Lubian, Elisa; Pavan, M. Phani
  • New Journal of Chemistry, Vol. 37, Issue 4
  • DOI: 10.1039/c3nj41161c

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

Photoreduction of zinc 8-vinylated chlorophyll derivative to bacteriochlorophyll-b/g analog possessing an 8-ethylidene group
journal, April 2013

  • Tamiaki, Hitoshi; Xu, Meiyun; Tanaka, Takuya
  • Bioorganic & Medicinal Chemistry Letters, Vol. 23, Issue 8
  • DOI: 10.1016/j.bmcl.2013.02.050

Refined syntheses of hydrodipyrrin precursors to chlorin and bacteriochlorin building blocks
journal, October 2009

  • Krayer, Michael; Balasubramanian, Thiagarajan; Ruzié, Christian
  • Journal of Porphyrins and Phthalocyanines, Vol. 13, Issue 10
  • DOI: 10.1142/S1088424609001406

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

Novel water-soluble 99mTc(I)/Re(I)-porphyrin conjugates as potential multimodal agents for molecular imaging
journal, May 2013


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

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

Photodynamic Effects of Novel XF Porphyrin Derivatives on Prokaryotic and Eukaryotic Cells
journal, March 2005


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

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

DNA-Binding Properties and Photocleavage Activity of Cationic Water-Soluble Chlorophyll Derivatives
journal, August 2006

  • Taima, Hidetoshi; Okubo, Akihiro; Yoshioka, Naoki
  • Chemistry - A European Journal, Vol. 12, Issue 24
  • DOI: 10.1002/chem.200501175

A New Approach to the Synthesis of N-Protected 2- and 5-Substituted 3-Halopyrroles
journal, March 1995


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

Studies of palladium-catalyzed coupling reactions for preparation of hindered 3-arylpyrroles relevant to (-)-rhazinilam and its analogues
journal, November 2001

  • Ghosez, Léon; Franc, Cécile; Denonne, Frédéric
  • Canadian Journal of Chemistry, Vol. 79, Issue 11
  • DOI: 10.1139/v01-156

Polymerization of Dyestuffs in Solution. Thionine and Methylene Blue 1
journal, January 1941

  • Rabinowitch, Eugene; Epstein, Leo F.
  • Journal of the American Chemical Society, Vol. 63, Issue 1
  • DOI: 10.1021/ja01846a011

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

An insight into solvent-free diimide porphyrin reduction: a versatile approach for meso-aryl hydroporphyrin synthesis
journal, January 2012

  • Pereira, Mariette M.; Abreu, Artur R.; Goncalves, Nuno P. F.
  • Green Chemistry, Vol. 14, Issue 6
  • DOI: 10.1039/c2gc35126a

Oxazolochlorins. 9. meso -Tetraphenyl-2-oxabacteriochlorins and meso -Tetraphenyl-2,12/13-dioxabacteriochlorins
journal, February 2013

  • Ogikubo, Junichi; Meehan, Eileen; Engle, James T.
  • The Journal of Organic Chemistry, Vol. 78, Issue 7
  • DOI: 10.1021/jo400031r

A convenient method for the synthesis of unsymmetrical 3,4-disubstituted pyrroles
journal, January 1990


Synthesis and Photophysical Characterization of Porphyrin, Chlorin and Bacteriochlorin Molecules Bearing Tethers for Surface Attachment
journal, November 2007


A compact water-soluble porphyrin bearing an iodoacetamido bioconjugatable site
journal, January 2008

  • Borbas, K. Eszter; Kee, Hooi Ling; Holten, Dewey
  • Org. Biomol. Chem., Vol. 6, Issue 1
  • DOI: 10.1039/B715072E

PEG-m-THPC–mediated Photodynamic Effects on Normal Rat Tissues¶
journal, January 2000


"Click chemistry" in the synthesis of the first glycoconjugates of bacteriochlorin series
journal, October 2012

  • Grin, Mikhail A.; Lonin, Ivan S.; Likhosherstov, Leonid M.
  • Journal of Porphyrins and Phthalocyanines, Vol. 16, Issue 10
  • DOI: 10.1142/S1088424612500848

Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures
journal, January 2013

  • Reddy, Kanumuri Ramesh; Jiang, Jianbing; Krayer, Michael
  • Chemical Science, Vol. 4, Issue 5
  • DOI: 10.1039/c3sc22317e

Design and synthesis of water-soluble polyaminated chlorins and bacteriochlorins – With near-infrared absorption
journal, September 2013


Photodynamic therapy of ovarian tumours and normal cells using 5,10,15,20-tetra-(3-carboxymethoxyphenyl)-chlorin
journal, March 1998


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

Amphiphilic chlorins and bacteriochlorins in micellar environments. Molecular design, de novo synthesis, and photophysical properties
journal, January 2013

  • Aravindu, Kunche; Mass, Olga; Vairaprakash, Pothiappan
  • Chemical Science, Vol. 4, Issue 9
  • DOI: 10.1039/c3sc51335a

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

Meso and β-pyrrole sulfonated porphyrins obtained by sulfonation of 5,15-bis(phenyl)porphyrin
journal, August 2000


Syntheses and properties of acetylene-linked bis- and trisporphyrins toward two-photon photodynamic therapy
journal, June 2007

  • Inaba, Yusuke; Ogawa, Kazuya; Kobuke, Yoshiaki
  • Journal of Porphyrins and Phthalocyanines, Vol. 11, Issue 06
  • DOI: 10.1142/S1088424607000461

2,6-Di-Butylpyridine—An Unusual Pyridine base
journal, August 1953

  • Brown, Herbert C.; Kanner, Bernard
  • Journal of the American Chemical Society, Vol. 75, Issue 15
  • DOI: 10.1021/ja01111a530

Long-Range Energy Propagation in Nanometer Arrays of Light Harvesting Antenna Complexes
journal, April 2010

  • Escalante, Maryana; Lenferink, Aufried; Zhao, Yiping
  • Nano Letters, Vol. 10, Issue 4, p. 1450-1457
  • DOI: 10.1021/nl1003569

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

Photodynamic therapy in the treatment of microbial infections: Basic principles and perspective applications
journal, January 2006

  • Jori, Giulio; Fabris, Clara; Soncin, Marina
  • Lasers in Surgery and Medicine, Vol. 38, Issue 5
  • DOI: 10.1002/lsm.20361

The Influence of Variation in Concentration on the Absorption Spectra of Dye Solutions.
journal, January 1924

  • Holmes, Walter C.
  • Industrial & Engineering Chemistry, Vol. 16, Issue 1
  • DOI: 10.1021/ie50169a014

Spectra of Molecular Complexes of Porphyrins in Aqueous Solution *
journal, September 1965


A Spectrophotometric Study of Thionine*
journal, January 1941

  • Epstein, Leo F.; Karush, Fred; Rabinowitch, Eugene
  • Journal of the Optical Society of America, Vol. 31, Issue 1
  • DOI: 10.1364/JOSA.31.000077

N-(Triisopropylsilyl)pyrrole. A progenitor "par excellence" of 3-substituted pyrroles
journal, December 1990

  • Bray, Brian L.; Mathies, Peter H.; Naef, Reto
  • The Journal of Organic Chemistry, Vol. 55, Issue 26
  • DOI: 10.1021/jo00313a019

Ultra-Violet Absorption Spectra in Relation to Physico-Chemical Processes
journal, March 1906

  • Baly, E. C. C.; Desch, C. H.
  • The Astrophysical Journal, Vol. 23
  • DOI: 10.1086/141309

Determination of the antibacterial efficacy of a new porphyrin-based photosensitizer against MRSA ex vivo
journal, January 2007

  • Maisch, T.; Bosl, C.; Szeimies, R. -M.
  • Photochemical & Photobiological Sciences, Vol. 6, Issue 5
  • DOI: 10.1039/b614770d


journal, October 2007


[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

Purpurinimide Carbohydrate Conjugates  Effect of the Position of the Carbohydrate Moiety in Photosensitizing Efficacy
journal, June 2007

  • Pandey, Suresh K.; Zheng, Xiang; Morgan, Janet
  • Molecular Pharmaceutics, Vol. 4, Issue 3, p. 448-464
  • DOI: 10.1021/mp060135x

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

Biomimetic Model of a Plant Photosystem Consisting of a Recombinant Light-Harvesting Complex and a Terrylene Dye
journal, September 2002


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


Design and synthesis of water-soluble bioconjugatable trans-AB-porphyrins
journal, December 2008


Synthesis of cationic water-soluble esters of chlorin e6
journal, June 2005



journal, August 2004


Stable Synthetic Cationic Bacteriochlorins as Selective Antimicrobial Photosensitizers
journal, July 2010

  • Huang, L.; Huang, Y. -Y.; Mroz, P.
  • Antimicrobial Agents and Chemotherapy, Vol. 54, Issue 9
  • DOI: 10.1128/AAC.00125-10

Integration of multiple chromophores with native photosynthetic antennas to enhance solar energy capture and delivery
journal, January 2013

  • Harris, Michelle A.; Parkes-Loach, Pamela S.; Springer, Joseph W.
  • Chemical Science, Vol. 4, Issue 10
  • DOI: 10.1039/c3sc51518d

Synthetic approaches for the conjugation of porphyrins and related macrocycles to peptides and proteins
journal, January 2011

  • Giuntini, Francesca; Alonso, Cristina M. A.; Boyle, Ross W.
  • Photochemical & Photobiological Sciences, Vol. 10, Issue 5
  • DOI: 10.1039/c0pp00366b

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

mTHPC Polymer Conjugates: The In Vivo Photodynamic Activity of Four Candidate Compounds
journal, March 1999

  • Grahn, M. F.; Giger, A.; McGuinness, A.
  • Lasers in Medical Science, Vol. 14, Issue 1
  • DOI: 10.1007/s101030050019

Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters
journal, November 1995

  • Ishiyama, Tatsuo; Murata, Miki; Miyaura, Norio
  • The Journal of Organic Chemistry, Vol. 60, Issue 23, p. 7508-7510
  • DOI: 10.1021/jo00128a024

Design, Synthesis, and Photophysical Characterization of Water-Soluble Chlorins
journal, April 2008

  • Borbas, K. Eszter; Chandrashaker, Vanampally; Muthiah, Chinnasamy
  • The Journal of Organic Chemistry, Vol. 73, Issue 8
  • DOI: 10.1021/jo7026728