Open-Chain Tetrapyrrole Spectra Database

OCTP212

PhotochemCAD ID	OCTP212

Absorption Spectrum

Absorption Wavelength	314
Absorption Epsilon	28200
Absorption Coefficient	28200 at 314 nm
Solvent	CH2Cl2
Reference	(Ituttaspe, 1993)
Spectrum Data	Download File

Fluorescence Spectrum

Solvent	CH2Cl2
Reference	(Ituttaspe, 1993)
Quantum Yield	Digitized from literature
Spectrum Data	Download File

"Absorption and fluorescence spectra of open-chain tetrapyrrole pigments-bilirubins, biliverdins, phycobilins, and synthetic analogues,"
Taniguchi, M.; Lindsey, J. S. J. Photochem. Photobiol. 2023, 55, 100585.

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[Antina, 2022]	L.A. Antina, A.A. Kalyagin, A.A. Ksenofontov, R.S. Pavelyev, O.A. Lodochnikova, D.R. Islamov, M.B. Berezin, E.V. Antina, Effects of ms-aryl substitution on the structure and spectral properties of new CH(Ar)-bis(BODIPY) luminophores, Spectrochim. Acta A Mol. Biomol. 265 (2022) 120393. https://doi.org/10.1016/j.saa.2021.120393
[Balch, 1993]	A.L. Balch, L. Latos-Grazynski, B.C. Noll, M.M. Olmstead, N. Safari, Isolation and characterization of an iron biliverdin-type complex that is formed along with verdohemochrome during the coupled oxidation of iron(II) octaethylporphyrin, J. Am. Chem. Soc. 115 (1993) 9056–9061. https://doi.org/10.1021/ja00073a022
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[Baudron, 2015]	S.A. Baudron, H. Ruffin, M.W. Hosseini, On Zn(II) 2,2′-bisdipyrrin circular helicates, Chem. Commun. 51 (2015) 5906–5909. https://doi.org/10.1039/C5CC00724K
[Bishop, 1991]	J.E. Bishop, J.O. Nagy, J.F. O'Connell, H. Rapoport, Diastereoselective synthesis of phycocyanobilin-cysteine adducts, J. Am. Chem. Soc. 113 (1991) 8024–8035. https://doi.org/10.1021/ja00021a032
[Boiadjiev, 2001]	S.E. Boiadjiev, D.A. Lightner, A water-soluble synthetic bilirubin with carboxyl groups replaced by sulfonyl moieties, Monatsh. Chem. 132 (2001) 1201–1212. https://doi.org/10.1007/s007060170035
[Boiadjiev, 2004]	S.E. Boiadjiev, D.A. Lightner, Conformational control by remote stereogenic centers: linear tetrapyrroles, Tetrahedron Asymm. 15 (2004) 3301–3305. https://doi.org/10.1016/j.tetasy.2004.08.029
[Boiadjiev, 2005]	S.E. Boiadjiev, D.A. Lightner, N21,N22-Carbonyl-bridged biliverdin. Red-blue color change effected by conformation, J. Heterocycl. Chem. 42 (2005) 161–164. https://doi.org/10.1002/jhet.5570420126
[Bonfiglio, 1982]	J.V. Bonfiglio, R. Bonnett, D.G. Buckley, D. Hamzetash, M.B. Hursthouse, K.M.A. Malik, S.C. Naithani, J. Trotter, The meso-reactivity of porphyrins and related compounds. Part VIII. Substitution and addition reactions of octaethyl-21H,24H-bilin-1,19-dione, a model verdin system. X-Ray analyses of octaethyl-5-nitro-21H,24H-bilin-1,19-dione and of 4,5-diethoxy-octaethyl-4,5-dihydro-21H,24H-bilin-1,19-dione, J. Chem. Soc., Perkin Trans. 1 (1982) 1291–1302. https://doi.org/10.1039/p19820001291
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[Braslavsky, 1991]	S.E. Braslavsky, D. Schneider, K. Heihoff, S. Nonell, P.F. Aramendia, K. Schaffner, Phytochrome models. 11. Photophysics and photochemistry of phycocyanobilin dimethyl ester, J. Am. Chem. Soc. 113 (1991) 7322–7334. https://doi.org/10.1021/ja00019a033
[Bröring, 2007]	M. Bröring, S. Link, C.D. Brandt, E.C. Tejero, Helical transition‐metal complexes of constrained 2,2′‐bidipyrrins, Eur. J. Inorg. Chem. 2007 (2007) 1661–1670. https://doi.org/10.1002/ejic.200600986
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[Brower, 2001]	J.O. Brower, D.A. Lightner, A.F. McDonagh, Aromatic congeners of bilirubin: Synthesis, stereochemistry, glucuronidation and hepatic transport, Tetrahedron 57 (2001) 7813–7827. https://doi.org/10.1016/S0040-4020(01)00773-6
[Brown, 1981]	S.B. Brown, J.A. Holroyd, R.F. Troxler, G.D. Offner, Bile pigment synthesis in plants. Incorporation of haem into phycocyanobilin and phycobiliproteins in Cyanidium caldarium, Biochem. J. 194 (1981) 137–147. https://doi.org/10.1042/bj1940137
[Carra, 1964]	P.Ó. Carra, C.Ó. hEocha, D.M. Carroll, Spectral properties of the phycobilins. II. Phycoerythrobilin, Biochemistry 3 (1964) 1343–1350. https://doi.org/10.1021/bi00897a026
[Chen, 1995a]	Q.-Q. Chen, H. Falk, On the chemistry of pyrrole pigments, XCIII: 1,2-bis-(dipyrrinon-9-ylidene)-ethane – a novel b-homoverdin chromophore, Monatsh. Chem. 126 (1995) 1097–1107. https://doi.org/10.1007/BF00811380
[Chen, 1995b]	Q.Q. Chen, H. Falk, On the chemistry of pyrrole pigments, XCIV: 1-(Dipyrrinon-9-yl)-3-(dipyrrinon-9-ylidene)-1-propene – a novel b-vinylogous verdin chromophore, Monatsh. Chem. 126 (1995) 1233–1244. https://doi.org/10.1007/BF00824302
[Chen, 1995c]	Q.-Q. Chen, H. Falk, On the chemistry of pyrrole pigments, XCV: 1,4-bis-(dipyrrinone-9-ylidene)-butene-2 – A novel b-homo-verdin chromophore, Monatsh. Chem. 126 (1995) 1323–1329. https://doi.org/10.1007/BF00807061
[Chen, 1999]	Q. Chen, M.T. Huggins, D.A. Lightner, W. Norona, A.F. McDonagh, Synthesis of a 10-oxo-bilirubin: Effects of the oxo group on conformation, transhepatic transport, and glucuronidation, J. Am. Chem. Soc. 121 (1999) 9253–9264. https://doi.org/10.1021/ja991814m
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[Chung, 2021]	D.T.M. Chung, P.V. Tran, K. Chau Nguyen, P. Wang, J.S. Lindsey, Synthesis of model bacteriochlorophylls containing substituents of native rings A, C and E, New J. Chem. 45 (2021) 13302–13316. https://doi.org/10.1039/D1NJ02469H.
[Crusats, 1998]	J. Crusats, A. Delgado, J.-A. Farrera, R. Rubires, J.M. Ribó, Solution structure of mesobilirubin XIIIα bridged between the propionic acid substituents, Monatsh. Chem. 129 (1998) 741–753. https://doi.org/10.1007/PL00013483
[Dolphin, 1966]	D. Dolphin, A.W. Johnson, J. Leng, P. van den Broek, The base-catalysed cyclisations of 1,19-dideoxybiladienes-ac, J. Chem. Soc., C (1966) 880–884. https://doi.org/10.1039/j39660000880
[Dudina, 2015]	N.A. Dudina, E.V. Antina, D.I. Sozonov, A.I. V'yugin, Effect of alkyl substitution in 3,3′-bis(dipyrrin) on chemosensor activity of fluorescent detection of Zn2+ cations, Russ. J. Org. Chem. 51 (2015) 1155–1161. https://doi.org/10.1134/S107042801508014X
[Edinger, 1984a]	J. Edinger, H. Falk, N. Müller, Zur chemie der pyrrolpigmente, 54. mitt.: Phytochrommodellstudien: Ein 2,3-dihydrobilatrien-abc-3-cholesterylderivat, Monatsh. Chem. 115 (1984) 837–852. https://doi.org/10.1007/BF01120979
[Edinger, 1984b]	J. Edinger, H. Falk, W. Jungwirth, N. Müller, U. Zrunek, Zur chemie der pyrrolpigmente, 56. mitt.: Phytochrommodellstudien: Die induzierten und natürlichen chiroptischen eigenschaften von bilatrienen-abc und 2,3-dihydrobilatrienen-abc, Monatsh. Chem. 115 (1984) 1081–1099. https://doi.org/10.1007/BF00798775
[Eivazi, 1977]	F. Eivazi, M.F. Hudson, K.M. Smith, Bile pigment studies III. Controlled oxidative degradation of 1,19(21,24)-bilindiones (bilitrienes), Tetrahedron 33 (1977) 2959–2964. https://doi.org/10.1016/0040-4020(77)88030-7
[Falk, 1978]	H. Falk, K. Grubmayr, E. Haslinger, T. Schlederer, K. Thirring, Beiträge zur chemie der pyrrolpigmente, 25. mitt.: Die diastereomeren (geometrisch isomeren) biliverdindimethylester – Struktur, konfiguration und konformation, Monatsh. Chem. 109 (1978) 1451–1473. https://doi.org/10.1007/BF00906057
[Falk, 1979a]	H. Falk, K. Thirring, Beiträge zur Chemie der pyrrolpigmente, XXXIII. Darstellung, struktur und eigenschaften von isomeren N-methyl-bilatrienen-abc (N-methyl-etiobiliverdine-IV-γ), Z. Naturforsch. B 34 (1979) 1448–1453. https://doi.org/10.1515/znb-1979-1020
[Falk, 1979b]	H. Falk, T. Schlederer, Beiträge zur Chemie der Pyrrolpigmente, XXX. Struktur und eigenschaften der laktimform eines bilatriens-abc (ätiobiliverdin-IV-γ), Liebigs Ann. Chem. 1979 (1979) 1560–1570. https://doi.org/10.1002/jlac.197919791015
[Falk, 1979c]	H. Falk, K. Thirring, Beiträge zur chemie der pyrrolpigmente, XXXIV. Über die konfiguration und konformation von diastereomeren N-methyl-O-methyl-bilatrienen-abc, Z. Naturforsch. B 34 (1979) 1600–1605. https://doi.org/10.1515/znb-1979-1123
[Falk, 1980a]	H. Falk, N. Müller, T. Schlederer, Beiträge zur chemie der pyrrolpigmente, 35. mitt.: Eine regioselektive, reversible addition an bilatriene-abc, Monatsh. Chem. 111 (1980) 159–175. https://doi.org/10.1007/BF00938725
[Falk, 1980b]	H. Falk, K. Thirring, Beiträge zur chemie der pyrrolpigmente, XXXVI. Zur anaeroben photochemie von 21.24-dimethy-aetiobiIiverdin-IV-γ, Z. Naturforsch. B 35 (1980) 376–380. https://doi.org/10.1515/znb-1980-0322
[Falk, 1981a]	H. Falk, T. Schlederer, P. Wolschann, Beiträge zur chemie der pyrrolpigmente, 38. mitt.: Zur assoziation von gallenpigmenten, Monatsh. Chem. 112 (1981) 199–207. https://doi.org/10.1007/BF00911086
[Falk, 1981b]	H. Falk, K. Thirring, Beiträge zur chemie der pyrrolpigmente-XXXVII: Überbrückte gallenpiqmente: N21-N24-methylen-aetiobiliverdin- IV-γ und N21-N24-methylen-aetiobilirubin-IV-γ, Tetrahedron 37 (1981) 761–766. https://doi.org/10.1016/S0040-4020(01)97694-X
[Falk, 1983]	H. Falk, U. Zrunek, Beiträge zur chemie der pyrrolpigmente, 50. mitt.: Phytochrommodellstudien: Das laktam – Laktimgleichgewicht des pyrrolidinonfragmentes von 2,3-dihydrobilatrienen-abc – Protonierungsgleichgewichte, Monatsh. Chem. 114 (1983) 983–998. https://doi.org/10.1007/BF00799958
[Falk, 1984a]	H. Falk, U. Zrunek, Beiträge zur chemie der pyrrolpigmente, 52. mitt.: Phytochrommodellstudien: Eine reversible addition an Δ-4 von 2,3-dihydrobilatrienen-abc, Monatsh. Chem. 115 (1984) 101–111. https://doi.org/10.1007/BF00798426
[Falk, 1984b]	H. Falk, P. Wolschann, U. Zrunek, Beiträge zur chemie der pyrrolpigmente, 53. mitt.: Phytochrommodellstudien: Das säure-basen-gleichgewicht diastereomerer 2,3-dihydrobilatriene-abc, Monatsh. Chem. 115 (1984) 243–249. https://doi.org/10.1007/BF00798415
[Falk, 1985a]	H. Falk, H. Gsaller, E. Hubauer, N. Müller, Beiträge zur chemie der pyrrolpigmente, 61. mitt.: Phytochrommodellstudien – Absorptionsspektren und strukturelle aspekte von 2,3-dihydrobilatrienen-abc aus der sicht eines semiempirischen quantenchemischen verfahrens (PPP-SCF-LCAO-MO-CI), Monatsh. Chem. 116 (1985) 939–959. https://doi.org/10.1007/BF00809188
[Falk, 1985b]	H. Falk, N. Müller, S. Wansch, Zur chemie der pyrrolpigmente, 63. mitt.: Phytochrommodellstudien: Das system 2,3-dihydrobilatrien – Hexamethylphosphorsäuretriamid als modell für gestreckte chromophore, Monatsh. Chem. 116 (1985) 1087–1097. https://doi.org/10.1007/BF00809199
[Falk, 1985c]	H. Falk, H. Flödl, Beiträge zur chemie der pyrrolpigmente, 64. mitt.: 2,3,7,8,12,13,17,18,22,23-Decamethyl-1,24,25,29-tetrahydro-27H-pentapyrrin-1,24-dion, der erste vertreter linearer pentapyrrole: Darstellung und struktur im gelösten zustand, Monatsh. Chem. 116 (1985) 1177–1187. https://doi.org/10.1007/BF00811251
[Falk, 1986a]	H. Falk, H. Flödl, Beiträge zur chemie der pyrrolpigmente, 65. mitt.: 2,3,7,8,12,13,17,18,22,23-Decamethyl-1,24,25,29-tetrahydro-27H-pentapyrrin-1,24-dion, der erste vertreter linearer pentapyrrole: Eigenschaften und reaktionsweisen, Monatsh. Chem. 117 (1986) 57–67. https://doi.org/10.1007/BF00809173
[Falk, 1986b]	H. Falk, A. Hinterberger, Beiträge zur chemie der pyrrolpigmente, 67. mitt.: Bilatriene-abc und 2,3-dihydrobilatriene-abc in micellaren systemen, Monatsh. Chem. 117 (1986) 1081–1090. https://doi.org/10.1007/BF00811278
[Falk, 1988a]	H. Falk, W. Medinger, N. Müller, Beiträge zur chemie der pyrrolpigmente, 75. mitt. Phytochrom-modell-studien: Stereochemische untersuchungen an einem zwischen den pyrrolischen ringen A und C peptidartig überbrückten 2,3-dihydrobilatrien-abc, Monatsh. Chem. 119 (1988) 113–126. https://doi.org/10.1007/BF00810093
[Falk, 1988b]	H. Falk, H. Flödl, U.G. Wagner, Beiträge zur chemie der pyrrolpigmente, 77. mitt. Synthese und struktur von b-Nor-bilatrienen-abc und b-Nor-biladienen-ac bzw. Bi-9,9′-dipyrrinonylidenen und bi-9,9′-dipyrrinonylenen, Monatsh. Chem. 119 (1988) 739–749. https://doi.org/10.1007/BF00809688
[Falk, 1989a]	H. Falk, N. Müller, H. Wöss, Beiträge zur chemie der pyrrolpigmente, 79. mitt.: Zum strukturellen einfluß stark raumerfüllender reste bei 10-substituierten 1,19-bilindionen, Monatsh. Chem. 120 (1989) 35–43. https://doi.org/10.1007/BF00809647
[Falk, 1989b]	H. Falk, K. Grubmayr, M. Marko, Beiträge zur chemie der pyrrolpigmente, 82. mitt.: Wasserlösliche polymere mit kovalent gebundenen violinoiden und 2,3-dihydro-verdinoiden gallenfarbstoffen, Monatsh. Chem. 120 (1989) 771–779. https://doi.org/10.1007/BF00809971
[Falk, 1990]	H. Falk, H. Wöss, Beiträge zur chemie der pyrrolpigmente, 83. mitt.: Zum einfluß geladener zentren auf die absorptionsspektren von 1,19-bilindionen, Monatsh. Chem. 121 (1990) 59–66. https://doi.org/10.1007/BF00810295
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