Synthesis and Spectral Properties of meso-Arylbacteriochlorins, Including Insights into Essential Motifs of their Hydrodipyrrin Precursors

Reddy, Muthyala Nagarjuna; Zhang, Shaofei; Kim, Han-Je; Mass, Olga; Taniguchi, Masahiko; Lindsey, Jonathan

doi:10.3390/molecules22040634

Title: Synthesis and Spectral Properties of meso-Arylbacteriochlorins, Including Insights into Essential Motifs of their Hydrodipyrrin Precursors

Journal Article · Fri Apr 14 00:00:00 EDT 2017 · Molecules

DOI: https://doi.org/10.3390/molecules22040634 · OSTI ID:1429912

Reddy, Muthyala Nagarjuna ^[1]; Zhang, Shaofei ^[2]; Kim, Han-Je ^[3]; Mass, Olga ^[2]; Taniguchi, Masahiko ^[2]; Lindsey, Jonathan ^[2]

North Carolina State Univ., Raleigh, NC (United States). Department of Chemistry; North Carolina State University at Chapel Hill
North Carolina State Univ., Raleigh, NC (United States). Department of Chemistry
Gongju National University of Education (Korea). Department of Science Education

Synthetic bacteriochlorins—analogues of bacteriochlorophylls, Nature’s near-infrared absorbers—are attractive for diverse photochemical studies. meso-Arylbacteriochlorins have been prepared by the self-condensation of a dihydrodipyrrin–carbinol or dihydrodipyrrin–acetal following an Eastern-Western (E-W) or Northern-Southern (N-S) joining process. The bacteriochlorins bear a gem-dimethyl group in each pyrroline ring to ensure stability toward oxidation. The two routes differ in the location of the gem-dimethyl group at the respective 3- or 2-position in the dihydrodipyrrin, and the method of synthesis of the dihydrodipyrrin. Treatment of a known 3,3-dimethyldihydrodipyrrin-1-carboxaldehyde with an aryl Grignard reagent afforded the dihydrodipyrrin-1-(aryl)carbinol, and upon subsequent acetylation, the corresponding dihydrodipyrrin-1-methyl acetate (dihydrodipyrrin– acetate). Self-condensation of the dihydrodipyrrin–acetate gave a meso-diarylbacteriochlorin (E-W route). A 2,2-dimethyl-5-aryldihydrodipyrrin-1-(aryl)carbinol underwent self-condensation to give a trans-A₂B₂-type meso-tetraarylbacteriochlorin (N-S route). In each case, the aromatization process entails a 2e^-/2H⁺ (aerobic) dehydrogenative oxidation following the dihydrodipyrrin self-condensation. Comparison of a tetrahydrodipyrrin–acetal (0%) versus a dihydrodipyrrin–acetal (41%) in bacteriochlorin formation and results with various 1-substituted dihydrodipyrrins revealed the importance of resonance stabilization of the reactive hydrodipyrrin intermediate. Altogether 10 new dihydrodipyrrins and five new bacteriochlorins have been prepared. The bacteriochlorins exhibit characteristic bacteriochlorophyll-like absorption spectra, including a Q_y band in the region 726–743 nm.

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Research Organization:: Univ. of North Carolina, Chapel Hill, NC (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: FG02-05ER15651

OSTI ID:: 1429912

Journal Information:: Molecules, Journal Name: Molecules Journal Issue: 4 Vol. 22; ISSN MOLEFW; ISSN 1420-3049

Publisher:: MDPICopyright Statement

Country of Publication:: United States

Language:: English

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De novo synthesis and photophysical characterization of annulated bacteriochlorins. Mimicking and extending the properties of bacteriochlorophylls Krayer, Michael; Yang, Eunkyung; Diers, James R. New Journal of Chemistry, Vol. 35, Issue 3, p. 587-601 https://doi.org/10.1039/c0nj00771d	journal	January 2011
Correlation of photophysical parameters with macrocycle distortion in porphyrins with graded degree of saddle distortion Röder, Beate; Büchner, Maren; Rückmann, Ilja Photochemical & Photobiological Sciences, Vol. 9, Issue 8 https://doi.org/10.1039/c0pp00107d	journal	January 2010
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Effects of Strong Electronic Coupling in Chlorin and Bacteriochlorin Dyads Kang, Hyun Suk; Esemoto, Nopondo N.; Diers, James R. The Journal of Physical Chemistry A, Vol. 120, Issue 3 https://doi.org/10.1021/acs.jpca.5b10686	journal	January 2016
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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
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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
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Bismuth-Catalyzed Intramolecular Carbo-oxycarbonylation of 3-Alkynyl Esters Komeyama, Kimihiro; Takahashi, Keita; Takaki, Ken Organic Letters, Vol. 10, Issue 22 https://doi.org/10.1021/ol8019567	journal	November 2008
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De novo synthesis and photophysical characterization of annulated bacteriochlorins. Mimicking and extending the properties of bacteriochlorophylls Krayer, Michael; Yang, Eunkyung; Diers, James R. New Journal of Chemistry, Vol. 35, Issue 3, p. 587-601 https://doi.org/10.1039/c0nj00771d	journal	January 2011
Correlation of photophysical parameters with macrocycle distortion in porphyrins with graded degree of saddle distortion Röder, Beate; Büchner, Maren; Rückmann, Ilja Photochemical & Photobiological Sciences, Vol. 9, Issue 8 https://doi.org/10.1039/c0pp00107d	journal	January 2010
Synthetic bacteriochlorins with integral spiro-piperidine motifs Reddy, Kanumuri Ramesh; Lubian, Elisa; Pavan, M. Phani New Journal of Chemistry, Vol. 37, Issue 4 https://doi.org/10.1039/c3nj41161c	journal	January 2013
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Annulated bacteriochlorins for near-infrared photophysical studies Fujita, Hikaru; Jing, Haoyu; Krayer, Michael New Journal of Chemistry, Vol. 43, Issue 19 https://doi.org/10.1039/c9nj01113g	journal	January 2019

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Title: Synthesis and Spectral Properties of meso-Arylbacteriochlorins, Including Insights into Essential Motifs of their Hydrodipyrrin Precursors

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