Synthesis of bacteriochlorins bearing diverse β-substituents

Jing, Haoyu; Wang, Pengzhi; Chen, Boyang; Jiang, Jianbing; Vairaprakash, Pothiappan; Liu, Sijia; Rong, Jie; Chen, Chih-Yuan; Nalaoh, Phattananawee; Lindsey, Jonathan S.

doi:10.1039/d1nj05852e

Synthesis of bacteriochlorins bearing diverse β-substituents

Journal Article · Wed Mar 02 00:00:00 EST 2022 · New Journal of Chemistry

DOI:https://doi.org/10.1039/d1nj05852e· OSTI ID:1978808

Jing, Haoyu ^[1]; Wang, Pengzhi ^[2]; Chen, Boyang ^[2]; ^[2]; ^[2]; Liu, Sijia ^[2]; ^[2]; Chen, Chih-Yuan ^[2]; Nalaoh, Phattananawee ^[3]; ^[2]

North Carolina State University, Raleigh, NC (United States); OSTI
North Carolina State University, Raleigh, NC (United States)
Vidyasirimedhi Institute of Science and Technology, Rayong (Thailand)

Synthetic bacteriochlorins, analogues of native bacteriochlorophylls, provide absorption in the near-infrared spectral region and hence are valuable for fundamental studies in photochemistry and applications ranging from solar energy conversion to photomedicine. The full realization of such opportunities hinges on access to synthetically malleable bacteriochlorins. Here, two established routes that rely on self-condensation of a dihydrodipyrrin-acetal or dihydrodipyrrin-carboxaldehyde have been exploited to prepare 6 bacteriochlorins (2 new, 4 known in improved fashion). Each bacteriochlorin contains a gem-dimethyl group in the reduced, pyrroline ring to ensure stability toward adventitious dehydrogenation. These and related synthetic bacteriochlorins have been derivatized to tailor the perimeter of the macrocycle with diverse groups, affording 9 additional new bacteriochlorins and 4 known bacteriochlorins. By direct installation and/or derivatization, the scope of attached entities in this collection includes alkyl, amino, aryl, bromo, carboethoxy, oxo, phenylethynyl, and pyridyl. Furthermore, the bacteriochlorins are suited for surface attachment, bioconjugation, water-solubilization, vibrational studies, and elaboration into multichromophore arrays. Altogether the synthesis of 25 new compounds (11 bacteriochlorins, 14 precursors) is described.

View Accepted Manuscript (DOE)

Research Organization:: Washington University, St. Louis, MO (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC)

Grant/Contract Number:: FG02-05ER15661

OSTI ID:: 1978808

Alternate ID(s):: OSTI ID: 1847027

Journal Information:: New Journal of Chemistry, Journal Name: New Journal of Chemistry Journal Issue: 12 Vol. 46; ISSN NJCHE5; ISSN 1144-0546

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (80)

Investigation of MALDI-TOF Mass Spectrometry of Diverse Synthetic Metalloporphyrins, Phthalocyanines and Multiporphyrin Arrays Srinivasan, N.; Haney, Carol A.; Lindsey, Jonathan S. Journal of Porphyrins and Phthalocyanines, Vol. 03, Issue 04 https://doi.org/10.1002/(SICI)1099-1409(199904)3:4<283::AID-JPP132>3.0.CO;2-F	journal	April 1999
Total Synthesis of the Proposed Structure of (+)-Tolyporphin AO,O-Diacetate Minehan, Thomas G.; Kishi, Yoshito Angewandte Chemie International Edition, Vol. 38, Issue 7 https://doi.org/10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7	journal	April 1999
Radiolabelled porphyrins in nuclear medicine: A review of the role of porphyrins in PET and SPECT imaging Waghorn, Philip A. Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 57, Issue 4 https://doi.org/10.1002/jlcr.3166	journal	December 2013
Spectroscopy and Structure Determination Kobayashi, Masami; Akiyama, Machiko; Kano, Hiromi Advances in Photosynthesis and Respiration https://doi.org/10.1007/1-4020-4516-6_6	book	January 2007
Chemical transformations of bacteriochlorophyll a and its medical applications Grin, M. A.; Mironov, A. F. Russian Chemical Bulletin, Vol. 65, Issue 2 https://doi.org/10.1007/s11172-016-1307-1	journal	February 2016
Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998 Suzuki, Akira Journal of Organometallic Chemistry, Vol. 576, Issue 1-2 https://doi.org/10.1016/S0022-328X(98)01055-9	journal	March 1999
The Henry reaction: recent examples Luzzio, Frederick A. Tetrahedron, Vol. 57, Issue 6 https://doi.org/10.1016/S0040-4020(00)00965-0	journal	February 2001
A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines Sonogashira, Kenkichi; Tohda, Yasuo; Hagihara, Nobue Tetrahedron Letters, Vol. 16, Issue 50 https://doi.org/10.1016/S0040-4039(00)91094-3	journal	January 1975
A new and simple synthesis of the pyrrole ring system from Michael acceptors and tosylmethylisocyanides van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E. Tetrahedron Letters, Vol. 13, Issue 52 https://doi.org/10.1016/S0040-4039(01)85244-8	journal	January 1972
Bacteriochlorins and their metal complexes as NIR-absorbing photosensitizers: properties, mechanisms, and applications Pucelik, Barbara; Sułek, Adam; Dąbrowski, Janusz M. Coordination Chemistry Reviews, Vol. 416 https://doi.org/10.1016/j.ccr.2020.213340	journal	August 2020
Near-infrared emissive bacteriochlorin-diketopyrrolopyrrole triads: Synthesis and photophysical properties Ponsot, Flavien; Desbois, Nicolas; Bucher, Léo Dyes and Pigments, Vol. 160 https://doi.org/10.1016/j.dyepig.2018.08.059	journal	January 2019
Water soluble near infrared dyes based on PEGylated-Tetrapyrrolic macrocycles Pinto, Sara M. A.; Almeida, Sara F. F.; Tomé, Vanessa A. Dyes and Pigments, Vol. 195 https://doi.org/10.1016/j.dyepig.2021.109677	journal	November 2021
Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer Ogata, Fusa; Nagaya, Tadanobu; Maruoka, Yasuhiro Bioconjugate Chemistry, Vol. 30, Issue 1 https://doi.org/10.1021/acs.bioconjchem.8b00820	journal	November 2018
Synthesis of AD-Dihydrodipyrrins Equipped with Latent Substituents of Native Chlorophylls and Bacteriochlorophylls Wang, Pengzhi; Lindsey, Jonathan S. The Journal of Organic Chemistry, Vol. 86, Issue 17 https://doi.org/10.1021/acs.joc.1c01239	journal	August 2021
Northern–Southern Route to Synthetic Bacteriochlorins Liu, Yizhou; Lindsey, Jonathan S. The Journal of Organic Chemistry, Vol. 81, Issue 23 https://doi.org/10.1021/acs.joc.6b02334	journal	November 2016
Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles Meares, Adam; Satraitis, Andrius; Akhigbe, Joshua The Journal of Organic Chemistry, Vol. 82, Issue 12 https://doi.org/10.1021/acs.joc.7b00357	journal	June 2017
Design, Sustainable Synthesis, and Programmed Reactions of Templated N -Heteroaryl-Fused Vinyl Sultams Laha, Joydev K.; Sharma, Shubhra; Kirar, Seema The Journal of Organic Chemistry, Vol. 82, Issue 18 https://doi.org/10.1021/acs.joc.7b01340	journal	August 2017
BODIPY–Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands Meares, Adam; Satraitis, Andrius; Ptaszek, Marcin The Journal of Organic Chemistry, Vol. 82, Issue 24 https://doi.org/10.1021/acs.joc.7b02031	journal	November 2017
Photoisomerization of Enediynyl Linker Leads to Slipped Cofacial Hydroporphyrin Dyads with Strong Through-Bond and Through-Space Electronic Interactions Meares, Adam; Yu, Zhanqian; Viswanathan Bhagavathy, Ganga The Journal of Organic Chemistry, Vol. 84, Issue 12 https://doi.org/10.1021/acs.joc.9b00731	journal	May 2019
meso -Diphenylbacteriochlorins: Macrocyclic Dyes with Rare Colors for Dye-Sensitized Solar Cells Chakraborty, Subrata; You, Huei-Chi; Huang, Chung-Kai The Journal of Physical Chemistry C, Vol. 121, Issue 13 https://doi.org/10.1021/acs.jpcc.7b00097	journal	March 2017
Galactosyl Human Serum Albumin-NMP1 Conjugate: A Near Infrared (NIR)-Activatable Fluorescence Imaging Agent to Detect Peritoneal Ovarian Cancer Metastases Alexander, Vinita M.; Sano, Kohei; Yu, Zhanqian Bioconjugate Chemistry, Vol. 23, Issue 8 https://doi.org/10.1021/bc3002419	journal	July 2012
Activatable Organic Near-Infrared Fluorescent Probes Based on a Bacteriochlorin Platform: Synthesis and Multicolor in Vivo Imaging with a Single Excitation Harada, Toshiko; Sano, Kohei; Sato, Kazuhide Bioconjugate Chemistry, Vol. 25, Issue 2 https://doi.org/10.1021/bc4005238	journal	January 2014
The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry ^† Chinchilla, Rafael; Nájera, Carmen Chemical Reviews, Vol. 107, Issue 3 https://doi.org/10.1021/cr050992x	journal	March 2007
Synthesis and Photophysical Characterization of Stable Indium Bacteriochlorins Krayer, Michael; Yang, Eunkyung; Kim, Han-Je Inorganic Chemistry, Vol. 50, Issue 10 https://doi.org/10.1021/ic200325d	journal	May 2011
Synthesis and Physicochemical Properties of Metallobacteriochlorins Chen, Chih-Yuan; Sun, Erjun; Fan, Dazhong Inorganic Chemistry, Vol. 51, Issue 17 https://doi.org/10.1021/ic301262k	journal	August 2012
Tolyporphin, a novel multidrug resistance reversing agent from the blue-green alga Tolypothrix nodosa Prinsep, Michele R.; Caplan, Faith R.; Moore, Richard E. Journal of the American Chemical Society, Vol. 114, Issue 1 https://doi.org/10.1021/ja00027a072	journal	January 1992
Preparation and Reactions of 2,6-Di-t-butylpyridine and Related Hindered Bases. A Case of Steric Hindrance toward the Proton ^1,2 Brown, Herbert C.; Kanner, Bernard Journal of the American Chemical Society, Vol. 88, Issue 5 https://doi.org/10.1021/ja00957a023	journal	March 1966
Diimide reduction of porphyrins Whitlock, Howard W.; Hanauer, R.; Oester, M. Y. Journal of the American Chemical Society, Vol. 91, Issue 26 https://doi.org/10.1021/ja01054a044	journal	December 1969
Toward a General Synthesis of Chlorins O'Nea, William G.; Jacobi, Peter A. Journal of the American Chemical Society, Vol. 130, Issue 3 https://doi.org/10.1021/ja0780075	journal	January 2008
Design, Synthesis, and Photodynamics of Light-Harvesting Arrays Comprised of a Porphyrin and One, Two, or Eight Boron-Dipyrrin Accessory Pigments Li, Feirong; Yang, Sung Ik; Ciringh, Yangzhen Journal of the American Chemical Society, Vol. 120, Issue 39 https://doi.org/10.1021/ja9812047	journal	October 1998
Allylic oxidation with 3,5-dimethylpyrazole. Chromium trioxide complex steroidal .DELTA.5-7-ketones Salmond, William G.; Barta, Mary A.; Havens, Jeffrey L. The Journal of Organic Chemistry, Vol. 43, Issue 10 https://doi.org/10.1021/jo00404a049	journal	May 1978
De Novo Synthesis of Stable Tetrahydroporphyrinic Macrocycles: Bacteriochlorins and a Tetradehydrocorrin Kim, Han-Je; Lindsey, Jonathan S. The Journal of Organic Chemistry, Vol. 70, Issue 14 https://doi.org/10.1021/jo050467y	journal	July 2005
Studies in Chlorin Chemistry. II. A Versatile Synthesis of Dihydrodipyrrins O'Neal, William G.; Roberts, William P.; Ghosh, Indranath The Journal of Organic Chemistry, Vol. 70, Issue 18 https://doi.org/10.1021/jo050907l	journal	September 2005
Studies in Chlorin Chemistry. 3. A Practical Synthesis of C,D-Ring Symmetric Chlorins of Potential Utility in Photodynamic Therapy O'Neal, William G.; Roberts, William P.; Ghosh, Indranath The Journal of Organic Chemistry, Vol. 71, Issue 9 https://doi.org/10.1021/jo060041z	journal	April 2006
Synthetic Chlorins Bearing Auxochromes at the 3- and 13-Positions Laha, Joydev K.; Muthiah, Chinnasamy; Taniguchi, Masahiko The Journal of Organic Chemistry, Vol. 71, Issue 11 https://doi.org/10.1021/jo060208o	journal	May 2006
Regioselective 15-Bromination and Functionalization of a Stable Synthetic Bacteriochlorin Fan, Dazhong; Taniguchi, Masahiko; Lindsey, Jonathan S. The Journal of Organic Chemistry, Vol. 72, Issue 14 https://doi.org/10.1021/jo070785s	journal	July 2007
A trans-AB-Bacteriochlorin Building Block Mass, Olga; Lindsey, Jonathan S. The Journal of Organic Chemistry, Vol. 76, Issue 22, p. 9478-9487 https://doi.org/10.1021/jo201967k	journal	November 2011
Near-IR Emissive Chlorin–Bacteriochlorin Energy-Transfer Dyads with a Common Donor and Acceptors with Tunable Emission Wavelength Yu, Zhanqian; Ptaszek, Marcin The Journal of Organic Chemistry, Vol. 78, Issue 21 https://doi.org/10.1021/jo4016858	journal	October 2013
Strongly Conjugated Hydroporphyrin Dyads: Extensive Modification of Hydroporphyrins’ Properties by Expanding the Conjugated System Yu, Zhanqian; Pancholi, Chirag; Bhagavathy, Ganga Viswanathan The Journal of Organic Chemistry, Vol. 79, Issue 17 https://doi.org/10.1021/jo501041b	journal	August 2014
Tailoring a Bacteriochlorin Building Block with Cationic, Amphipathic, or Lipophilic Substituents Ruzié, Christian; Krayer, Michael; Balasubramanian, Thiagarajan The Journal of Organic Chemistry, Vol. 73, Issue 15 https://doi.org/10.1021/jo800736c	journal	August 2008
Design and Synthesis of Lamellarin D Analogues Targeting Topoisomerase I Ohta, Takeshi; Fukuda, Tsutomu; Ishibashi, Fumito The Journal of Organic Chemistry, Vol. 74, Issue 21 https://doi.org/10.1021/jo901589e	journal	September 2009
Expanded Scope of Synthetic Bacteriochlorins via Improved Acid Catalysis Conditions and Diverse Dihydrodipyrrin-Acetals Krayer, Michael; Ptaszek, Marcin; Kim, Han-Je The Journal of Organic Chemistry, Vol. 75, Issue 4, p. 1016-1039 https://doi.org/10.1021/jo9025572	journal	February 2010
Extending the Short and Long Wavelength Limits of Bacteriochlorin Near-Infrared Absorption via Dioxo- and Bisimide-Functionalization Vairaprakash, Pothiappan; Yang, Eunkyung; Sahin, Tuba The Journal of Physical Chemistry B, Vol. 119, Issue 12 https://doi.org/10.1021/jp512818g	journal	March 2015
Resonance Raman, Infrared, and Normal Coordinate Analysis of Free-Base Tetraphenylbacteriochlorin: A Model for Bacteriopheophytins Lin, Ching-Yao; Spiro, Thomas G. The Journal of Physical Chemistry B, Vol. 101, Issue 3 https://doi.org/10.1021/jp962479g	journal	January 1997
A New Synthesis of Chlorins Jacobi, Peter A.; Lanz, Sandra; Ghosh, Indranath Organic Letters, Vol. 3, Issue 6 https://doi.org/10.1021/ol006983m	journal	March 2001
Directed Lithiation of N -Benzenesulfonyl-3-bromopyrrole. Electrophile-Controlled Regioselective Functionalization via Dynamic Equilibrium between C-2 and C-5 Lithio Species Fukuda, Tsutomu; Ohta, Takeshi; Sudo, Ei-ichi Organic Letters, Vol. 12, Issue 12 https://doi.org/10.1021/ol100810c	journal	June 2010
Multifunctional Bacteriochlorins from Selective Palladium-Coupling Reactions Yu, Zhanqian; Ptaszek, Marcin Organic Letters, Vol. 14, Issue 14 https://doi.org/10.1021/ol3015545	journal	July 2012
Swallowtail Bacteriochlorins. Lipophilic Absorbers for the Near-Infrared Borbas, K. Eszter; Lindsey, Jonathan S. Organic Letters, Vol. 10, Issue 10 https://doi.org/10.1021/ol800436u	journal	May 2008
Synthesis and Structure of Tolyporphin A O,O -Diacetate Wang, Wengui; Kishi, Yoshito Organic Letters, Vol. 1, Issue 7 https://doi.org/10.1021/ol9902374	journal	October 1999
Flexible, Bowl-Shaped N-Heterocyclic Carbene Ligands: Substrate Specificity in Iridium-Catalyzed Ketone Hydrosilylation Chianese, Anthony R.; Mo, Allen; Datta, Dibyadeep Organometallics, Vol. 28, Issue 2 https://doi.org/10.1021/om800878m	journal	December 2008
Hydrophilic tetracarboxy bacteriochlorins for photonics applications Jiang, Jianbing; Vairaprakash, Pothiappan; Reddy, Kanumuri Ramesh Org. Biomol. Chem., Vol. 12, Issue 1 https://doi.org/10.1039/C3OB41791C	journal	January 2014
Polarity-tunable and wavelength-tunable bacteriochlorins bearing a single carboxylic acid or NHS ester. Use in a protein bioconjugation model system Jiang, Jianbing; Chen, Chih-Yuan; Zhang, Nuonuo New Journal of Chemistry, Vol. 39, Issue 1 https://doi.org/10.1039/C4NJ01340A	journal	January 2015
NIR bacteriochlorin chromophores accessed by Heck and Sonogashira cross-coupling reactions on a tetrabromobacteriochlorin derivative de Assis, Francisco F.; Ferreira, Marco A. B.; Brocksom, Timothy J. Organic & Biomolecular Chemistry, Vol. 14, Issue 4 https://doi.org/10.1039/C5OB02228B	journal	January 2016
Synthesis and photophysical characteristics of 2,3,12,13-tetraalkylbacteriochlorins Zhang, Shaofei; Kim, Han-Je; Tang, Qun New Journal of Chemistry, Vol. 40, Issue 7 https://doi.org/10.1039/C6NJ00517A	journal	January 2016
Synthesis, photophysics and electronic structure of oxobacteriochlorins Liu, Mengran; Chen, Chih-Yuan; Hood, Don New Journal of Chemistry, Vol. 41, Issue 10 https://doi.org/10.1039/C6NJ04135C	journal	January 2017
Synthesis and photophysical characterization of bacteriochlorins equipped with integral swallowtail substituents Liu, Yizhou; Allu, Srinivasarao; Nagarjuna Reddy, Muthyala New Journal of Chemistry, Vol. 41, Issue 11 https://doi.org/10.1039/C7NJ00499K	journal	January 2017
Iron-catalysed enantioselective Suzuki–Miyaura coupling of racemic alkyl bromides Iwamoto, Takahiro; Okuzono, Chiemi; Adak, Laksmikanta Chemical Communications, Vol. 55, Issue 8 https://doi.org/10.1039/C8CC09523J	journal	January 2019
Porphyrins as ligands for ⁶⁴ copper: background and trends Aguilar-Ortíz, Edgar; Jalilian, Amir R.; Ávila-Rodríguez, Miguel A. MedChemComm, Vol. 9, Issue 10 https://doi.org/10.1039/C8MD00263K	journal	January 2018
Total synthesis campaigns toward chlorophylls and related natural hydroporphyrins – diverse macrocycles, unrealized opportunities Liu, Yizhou; Zhang, Shaofei; Lindsey, Jonathan S. Natural Product Reports, Vol. 35, Issue 9 https://doi.org/10.1039/C8NP00020D	journal	January 2018
New molecular design for blue BODIPYs Wu, Zhiyuan; Fujita, Hikaru; Magdaong, Nikki Cecil M. New Journal of Chemistry, Vol. 43, Issue 19 https://doi.org/10.1039/C9NJ01114E	journal	January 2019
Synthesis, properties and photovoltaic performance in dye-sensitized solar cells of three meso -diphenylbacteriochlorins bearing a dual-function electron-donor Chakraborty, Subrata; Tsai, Ming-Chi; Su, Xin-De RSC Advances, Vol. 10, Issue 11 https://doi.org/10.1039/C9RA10113F	journal	January 2020
Synthesis and practical applications of 2-(2-nitroalkyl)pyrroles Palmieri, Alessandro; Petrini, Marino Organic & Biomolecular Chemistry, Vol. 18, Issue 24 https://doi.org/10.1039/D0OB00956C	journal	January 2020
Considerations of the biosynthesis and molecular diversity of tolyporphins Lindsey, Jonathan S. New Journal of Chemistry, Vol. 45, Issue 27 https://doi.org/10.1039/D1NJ01761F	journal	January 2021
Tolyporphins A–R, unusual tetrapyrrole macrocycles in a cyanobacterium from Micronesia, assessed quantitatively from the culture HT-58-2 O'Donnell, Timothy J.; Gurr, Joshua R.; Dai, Jingqiu New Journal of Chemistry, Vol. 45, Issue 26 https://doi.org/10.1039/D1NJ02108G	journal	January 2021
Synthesis of model bacteriochlorophylls containing substituents of native rings A, C and E Chung, Duy T. M.; Tran, Phuong Vy; Chau Nguyen, Khiem New Journal of Chemistry, Vol. 45, Issue 30 https://doi.org/10.1039/D1NJ02469H	journal	January 2021
Accessing the near-infrared spectral region with stable, synthetic, wavelength-tunable bacteriochlorins Taniguchi, Masahiko; Cramer, David L.; Bhise, Anil D. New Journal of Chemistry, Vol. 32, Issue 6 https://doi.org/10.1039/b717803d	journal	January 2008
Synthesis of chlorins, bacteriochlorins and their tetraaza analogues Dudkin, S. V.; Makarova, E. A.; Lukyanets, E. A. Russian Chemical Reviews, Vol. 85, Issue 7 https://doi.org/10.1070/RCR4565	journal	July 2016
Reduction of Chlorophyllides, Chlorophylls and Chlorophyll Derivatives by Sodium Borohydride. Holt, A. Stanley Plant Physiology, Vol. 34, Issue 3 https://doi.org/10.1104/pp.34.3.310	journal	May 1959
Crystal structures of 4-bromo-2-formyl-1-tosyl-1 H -pyrrole, ( E )-4-bromo-2-(2-nitrovinyl)-1-tosyl-1 H -pyrrole and 6-(4-bromo-1-tosylpyrrol-2-yl)-4,4-dimethyl-5-nitrohexan-2-one Kingsbury, Christopher J.; Sample, Harry C.; Senge, Mathias O. Acta Crystallographica Section E Crystallographic Communications, Vol. 77, Issue 4 https://doi.org/10.1107/S2056989021002280	journal	March 2021
Design features for optimization of tetrapyrrole macrocycles as antimicrobial and anticancer photosensitizers Martinez De Pinillos Bayona, Alejandra; Mroz, Pawel; Thunshelle, Connor Chemical Biology & Drug Design, Vol. 89, Issue 2 https://doi.org/10.1111/cbdd.12792	journal	February 2017
Photophysical Characterization of the Naturally Occurring Dioxobacteriochlorin Tolyporphin A and Synthetic Oxobacteriochlorin Analogues Hood, Don; Niedzwiedzki, Dariusz M.; Zhang, Ran Photochemistry and Photobiology, Vol. 93, Issue 5 https://doi.org/10.1111/php.12781	journal	July 2017
Fluorescence Assay for Tolyporphins Amidst Abundant Chlorophyll in Crude Cyanobacterial Extracts Nguyen, Kathy‐Uyen; Zhang, Ran; Taniguchi, Masahiko Photochemistry and Photobiology, Vol. 97, Issue 6 https://doi.org/10.1111/php.13474	journal	July 2021
Refined syntheses of hydrodipyrrin precursors to chlorin and bacteriochlorin building blocks Krayer, Michael; Balasubramanian, Thiagarajan; Ruzié, Christian Journal of Porphyrins and Phthalocyanines, Vol. 13, Issue 10 https://doi.org/10.1142/S1088424609001406	journal	October 2009
Fast, facile, base-free microwave-assisted metallation of bacteriochlorophylls and corresponding high yield synthesis of TOOKAD Cheng, Miffy. H. Y.; Cevallos, Alberto; Rajora, Maneesha A. Journal of Porphyrins and Phthalocyanines, Vol. 25, Issue 07n08 https://doi.org/10.1142/S1088424621500656	journal	May 2021
Weakly conjugated bacteriochlorin-bacteriochlorin dyad: Synthesis and photophysical properties Yu, Zhanqian; Uthe, Brian; Gelfand, Rachel Journal of Porphyrins and Phthalocyanines, Vol. 25, Issue 07n08 https://doi.org/10.1142/S1088424621500711	journal	June 2021
Vibrational Characteristics of Tetrapyrrolic Macrocycles Procyk, A. D.; Bocian, D. F. Annual Review of Physical Chemistry, Vol. 43, Issue 1 https://doi.org/10.1146/annurev.pc.43.100192.002341	journal	October 1992
Recent Advances in the Synthesis of Hydroporphyrins Galezowski, Michal; Gryko, Daniel Current Organic Chemistry, Vol. 11, Issue 15 https://doi.org/10.2174/138527207782023157	journal	October 2007
Riley Oxidation of Heterocyclic Intermediates on Paths to Hydroporphyrins—A Review Wang, Pengzhi; Lindsey, Jonathan S. Molecules, Vol. 25, Issue 8 https://doi.org/10.3390/molecules25081858	journal	April 2020
4-Alkynoic Acids in the Synthesis of Biologically Important Tetrapyrroles A. Jacobi, Peter; L. Brielmann, Harry; Chiu, Melanie HETEROCYCLES, Vol. 82, Issue 2 https://doi.org/10.3987/REV-10-SR(E)6	journal	January 2010
Cycloaddition reactions of porphyrins Cavaleiro, José A. S.; Neves, Maria G. P. M. S.; Tomé, Augusto C. Arkivoc, Vol. 2003, Issue 14 https://doi.org/10.3998/ark.5550190.0004.e11	journal	October 2003

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Synthesis of bacteriochlorins bearing diverse β-substituents

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