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De Novo Synthesis of Bacteriochlorins Bearing Four Trideuteriomethyl Groups
| Content Provider | MDPI |
|---|---|
| Author | Jing, Haoyu Tang, Qun Bocian, David F. Lindsey, Jonathan S. |
| Copyright Year | 2022 |
| Description | Site-specific introduction of isotopes in tetrapyrrole macrocycles provides the foundation for probing physicochemical features germane to photosynthetic energy-transduction processes, but has chiefly been done with porphyrins rather than the more biologically relevant hydroporphyrin analogues of native photosynthetic pigments. A prior study incorporated pairwise$ ^{13}$C or$ ^{15}$N atoms in the skeleton of a bacteriochlorin containing a gem-dimethyl group in each pyrroline ring. Here, a complementary effort is reported that installs deuterium atoms in substituents at the perimeter of a bacteriochlorin. Thus, perdeuteriated 3-methyl-2,4-pentanedione was converted in an 8-step synthesis via the intermediacy of tert-butyl 5-formyl-3,4-bis(trideuteriomethyl)pyrrole-2-carboxylate to the 2,3,12,13-tetrakis(trideuteriomethyl)-8,8,18,18-tetramethylbacteriochlorin (BC-2). The fidelity of isotope substitution was maintained throughout the synthesis. Resonance Raman spectroscopy of the copper chelate (CuBC-2) revealed that addition of the four β-pyrrolic substituents alone is not sufficient to account for the vibronic complexity observed for the copper chelate of bacteriochlorophyll a (CuBChl a). The increased vibronic activity exhibited by the natural pigments and CuBChl a must arise from the increased structural complexity of the macrocycle. |
| Ending Page | 37 |
| Page Count | 16 |
| Starting Page | 22 |
| e-ISSN | 2673401X |
| DOI | 10.3390/org3010002 |
| Journal | Organics |
| Issue Number | 1 |
| Volume Number | 3 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2022-02-07 |
| Access Restriction | Open |
| Subject Keyword | Organics Plant Sciences Bacteriochlorophyll Isotopic Labeling Photosynthesis Pyrrole Synthesis Resonance Raman Spectroscopy |
| Content Type | Text |
| Resource Type | Article |
