Chlorin

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Not to be confused with chlorine.
Chlorin
Chlorin.svg
Names
Other names
2,3-Dihydroporphine
Identifiers
  • 2683-84-3 checkY
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C20H16N4/c1-2-14-10-16-5-6-18(23-16)12-20-8-7-19(24-20)11-17-4-3-15(22-17)9-13(1)21-14/h1-6,9-12,22-23H,7-8H2/b13-9-,14-10-,15-9-,16-10-,17-11-,18-12-,19-11-,20-12- checkY
    Key: UGADAJMDJZPKQX-CEVVSZFKSA-N checkY
  • InChI=1/C20H16N4/c1-2-14-10-16-5-6-18(23-16)12-20-8-7-19(24-20)11-17-4-3-15(22-17)9-13(1)21-14/h1-6,9-12,22-23H,7-8H2/b13-9-,14-10-,15-9-,16-10-,17-11-,18-12-,19-11-,20-12-
    Key: UGADAJMDJZPKQX-CEVVSZFKBJ
  • C(N1)(/C=C2N=C(C=C\2)/C=C3N/C(C=C\3)=C\4)=CC=C1/C=C5CCC4=N/5
Properties
C20H16N4
Molar mass 312.36784
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N  (what is checkY☒N ?)
Infobox references

In organic chemistry, chlorins are tetrapyrrole pigments that are partially hydrogenated porphyrins.[1] The parent chlorin is an unstable compound which undergoes air oxidation to porphine.

The name chlorin derives from chlorophyll. Chlorophylls are magnesium-containing chlorins and occur as photosynthetic pigments in chloroplasts. The reduced chlorin variants are present in bacteriochlorophylls and are named ‘bacteriochlorins’ and ‘isobacteriochlorins’.

Structures comparing porphin, chlorin, bacteriochlorin, and isobacteriochlorin.

Chlorins are excellent photosensitizing agents. Various synthetic chlorins analogues such as m-tetrahydroxyphenylchlorin (mTHPC) and mono-L-aspartyl chlorin e6 are effectively employed in experimental photodynamic therapy as photosensitizer.[2]

Natural Chlorins[]

Chlorophyll[]

The most abundant chlorin is the photosynthetic pigment chlorophyll. There are different types of chlorophylls, such as Chlorophyll a, Chlorophyll b, Chlorophyll d, Chlorophyll e, Chlorophyll f, Chlorophyll g. The basic unit of these chlorophylls is a chlorin with magnesium as a central metal atom.[3]

Contracted Chlorins[]

The contracted chlorins were reported as B(III)subchlorins in 2008, were synthesised by reduction of B(III)subporphyrin or by oxidation of corresponding B(III)subbacteriochlorin.[4] The B(III)subchlorins were directly synthesized as meso-ester B(III)subchlorin from meso-diester tripyrromethane, these class of compound showed very good fluorescence quantum yield and singlet oxygen producing efficiency[5][6]

See also[]

Further reading[]

  • Juse´lius, Jonas; Sundholm, Dage (2000). "The aromatic pathways of porphins, chlorins and bacteriochlorins". Physical Chemistry Chemical Physics. 2 (10): 2145–2151. Bibcode:2000PCCP....2.2145J. doi:10.1039/b000260g.

References[]

  1. ^ Gerard P. Moss (1988). "Nomenclature of Tetrapyrroles. Recommendations 1986". European Journal of Biochemistry. 178 (2): 277–328. doi:10.1111/j.1432-1033.1988.tb14453.x. PMID 3208761.
  2. ^ Spikes, John D. (July 1990). "New trends in photobiology". Journal of Photochemistry and Photobiology B: Biology. 6 (3): 259–274. doi:10.1016/1011-1344(90)85096-F. PMID 2120404.
  3. ^ K. Eszter, Borbas. Handbook of Porphyrin Science: 181: Chlorins. worldscientific. doi:10.1142/9789813149564_0001. ISBN 9814322326.
  4. ^ Osuka, Atsuhiro; Kim, Dongho. "Synthesis and Characterization of meso-Aryl-Substituted Subchlorins". Journal of the American Chemical Society. 130 (2): 438. doi:10.1021/ja078042b.
  5. ^ "Meso-Free Boron(III)subchlorin and Its μ-Oxo Dimer with Interacting Chromophores". Organic Letters. 22 (24): 9735. 3 Dec 2020. doi:10.1021/acs.orglett.0c03813.
  6. ^ "A2B- and A3-Type Boron(III)Subchlorins Derived from meso-Diethoxycarbonyltripyrrane: Synthesis and Photophysical Exploration". The Journal of Organic Chemistry. 15 Jul 2021. doi:10.1021/acs.joc.1c01001.
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