Open-Chain Tetrapyrrole Spectra Database

OCTP013a

PhotochemCAD ID	OCTP013a

Absorption Spectrum

Absorption Wavelength	442
Absorption Epsilon	33500
Absorption Coefficient	33500 at 442 nm
Solvent	CHCl3
Reference	(Boiadjiev, 2004)
Spectrum Data	Download File

Fluorescence Spectrum

Solvent	CHCl3
Reference	(Boiadjiev, 2004)
Quantum Yield	0.09
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.

[Akasaka, 2009]	H. Akasaka, H. Yukutake, Y. Nagata, T. Funabiki, T. Mizutani, H. Takagi, Y. Fukushima, L.R. Juneja, H. Nanbu, K. Kitahata, Selective adsorption of biladien-ab-one and zinc biladien-ab-one to mesoporous silica, Micropor. Mesopor. Mat. 120 (2009) 331–338. https://doi.org/10.1016/j.micromeso.2008.11.025
[Allik, 1994]	T.H. Allik, R.E. Hermes, G. Sathyamoorthi, J.H. Boyer, Spectroscopy and laser performance of new BF2-complex dyes in solution, Proc. SPIE 2115 (1994) 240–248. https://doi.org/10.1117/12.172742
[Antina, 2009]	E.V. Antina, G.B. Guseva, N.A. Dudina, A.I. V'yugin, A.S. Semeikin, Synthesis and spectral analysis of alkyl-substituted 3,3′-bis(dipyrrolylmethenes), Russ. J. Gen. Chem. 79 (2009) 2425–2434. https://doi.org/10.1134/S1070363209110243
[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
[Balch, 1994]	A.L. Balch, M. Mazzanti, B.C. Noll, M.M. Olmstead, Coordination patterns for biliverdin-type ligands. Helical and linked helical units in four-coordinate cobalt and five-coordinate manganese(III) complexes of octaethylbilindione, J. Am. Chem. Soc. 116 (1994) 9114–9122. https://doi.org/10.1021/ja00099a029
[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
[Bonfiglio, 1983]	J.V. Bonfiglio, R. Bonnett, D.G. Buckley, D. Hamzetash, M.B. Hursthouse, K.M.A. Malik, A.F. McDonagh, J. Trotter, Linear tetrapyrroles as ligands: Syntheses and X-ray analyses of boron and nickel complexes of octaethyl-21H,24H-bilin-1,19-dione, Tetrahedron. 39 (1983) 1865–1874. https://doi.org/10.1016/S0040-4020(01)88700-7
[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
[Bröring, 2008]	M. Bröring, S. Köhler, S. Link, O. Burghaus, C. Pietzonka, H. Kelm, H.-J. Krüger, Iron chelates of 2,2′-bidipyrrin: Stable analogues of the labile iron bilins, Chem. Eur. J. 14 (2008) 4006–4016. https://doi.org/10.1002/chem.200701919
[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
[Cheng, 1990]	L.-J. Cheng, J.-S. Ma, L.-C.C. (Li-J. Jiang), The complexes formed by biladiene a, b compounds with zinc ions and their application in determination of the chromophore composition of α- and β- subunits of R-phycoerythrin, Photochem. Photobiol. 52 (1990) 1071–1076. https://doi.org/10.1111/j.1751-1097.1990.tb08447.x
[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
[Falk, 1992]	H. Falk, M. Frühwirth, On the chemistry of pyrrole pigments, LXXXIX: Vinylogous linear di- and tetrapyrroles, Monatsh. Chem. 123 (1992) 1213–1221. https://doi.org/10.1007/BF00808284
[Falk, 1993]	H. Falk, A. Šuste, On the chemistry of pyrrole pigments, XC: Pyridinologous linear tri- and tetrapyrroles, Monatsh. Chem. 124 (1993) 881–891. https://doi.org/10.1007/BF00816411
[Fuhrhop, 1974]	J.-H. Fuhrhop, PeterK.W. Wasser, J. Subramanian, U. Schrader, Formylbiliverdine und ihre Metallkomplexe, Liebigs Ann. Chem. 1974 (1974) 1450–1466. https://doi.org/10.1002/jlac.197419740909
[Fuhrhop, 1975]	J.-H. Fuhrhop, A. Salek, J. Subramanian, C. Mengersen, S. Besecke, Metallkomplexe von biliverdinderivaten, Liebigs Ann. Chem. 1975 (1975) 1131–1147. https://doi.org/10.1002/jlac.197519750612
[Ghidinelli, 2018]	S. Ghidinelli, S. Abbate, S.E. Boiadjiev, D.A. Lightner, G. Longhi, l -Stercobilin-HCl and d-urobilin-HCl. analysis of their chiroptical and conformational properties by VCD, ECD, and CPL experiments and MD and DFT calculations, J. Phys. Chem. B 122 (2018) 12351–12362. https://doi.org/10.1021/acs.jpcb.8b07954
[Ghosh, 2004]	B. Ghosh, D.A. Lightner, A.F. McDonagh, Synthesis, conformation, and metabolism of a selenium bilirubin, Monatsh. Chem. 135 (2004) 1189–1199. https://doi.org/10.1007/s00706-004-0191-9
[Gossauer, 1974]	A. Gossauer, W. Hirsch, Synthesen von Gallenfarbstoffen, IV. Totalsynthese des racemischen phycocyanobilins (phycobiliverdins) sowie eines “homophycobiliverdins,” Liebigs Ann. Chem. 1974 (1974) 1496–1513. https://doi.org/10.1002/jlac.197419740913
[Guseva, 2008]	G.B. Guseva, N.A. Dudina, E.V. Antina, A.I. V'yugin, A.S. Semeikin, 3,3′-bis(dipyrrolylmethenes) as new chelating ligands: Synthesis and spectral properties, Russ. J. Gen. Chem. 78 (2008) 1215–1224. https://doi.org/10.1134/S1070363208060200
[Guseva, 2019]	Galina.B. Guseva, E.V. Antina, A.A. Ksenofontov, The complex formation of indium(III) acetate with alkyl-substituted 3,3′-bis(dipyrromethene) ligands, Inorg. Chim. Acta 498 (2019) 119146. https://doi.org/10.1016/j.ica.2019.119146
[Huster, 1988]	M.S. Huster, K.M. Smith, Ring cleavage of chlorophyll derivatives: Isolation of oxochlorin intermediates and ring opening via a two oxygen molecule mechanism, Tetrahedron Lett. 29 (1988) 5707–5710. https://doi.org/10.1016/S0040-4039(00)82168-1
[Ituttaspe, 1993]	J. Ituttaspe, N. Engel, P. Matzinger, V. Mooser, A. Gossauer, Chlorophyll catabolism. Part 3. Structure elucidation and partial synthesis of a new red bilin derivative from Chlorella protothecoides, Photochem. Photobiol. 58 (1993) 116–119. https://doi.org/10.1111/j.1751-1097.1993.tb04911.x
[Johnson, 1999]	J.A. Johnson, M.M. Olmstead, A.L. Balch, Reactivity of the verdoheme analogues. Opening of the planar macrocycle by amide and thiolate nucleophiles to form helical complexes, Inorg. Chem. 38 (1999) 5379–5383. https://doi.org/10.1021/ic9904283
[Johnson, 2001]	J.A. Johnson, M.M. Olmstead, A.M. Stolzenberg, A.L. Balch, Ring-opening and meso substitution from the reaction of cyanide ion with zinc verdohemes, Inorg. Chem. 40 (2001) 5585–5595. https://doi.org/10.1021/ic0103300
[Kakeya, 2014]	K. Kakeya, M. Aozasa, T. Mizutani, Y. Hitomi, M. Kodera, Nucleophilic ring opening of meso-substituted 5-oxaporphyrin by oxygen, nitrogen, sulfur, and carbon nucleophiles, J. Org. Chem. 79 (2014) 2591–2600. https://doi.org/10.1021/jo5000412
[Koerner, 1998]	R. Koerner, M.M. Olmstead, A. Ozarowski, S.L. Phillips, P.M. Van Calcar, K. Winkler, A.L. Balch, Possible intermediates in biological metalloporphyrin oxidative degradation. Nickel, copper, and cobalt complexes of octaethylformybiliverdin and their conversion to a verdoheme, J. Am. Chem. Soc. 120 (1998) 1274–1284. https://doi.org/10.1021/ja973088y
[Kuenzle, 1970]	C.C. Kuenzle, Bilirubin conjugates of human bile. Nuclear-magnetic-resonance, infrared and optical spectra of model compounds, Biochem. J. 119 (1970) 395–409. https://doi.org/10.1042/bj1190395
[Kufer, 1983]	W. Kufer, H. Scheer, A.R. Holzwarth, Isophorcarubin – A conformationally restricted and highly fluorescent bilirubin, Isr. J. Chem. 23 (1983) 233–240. https://doi.org/10.1002/ijch.198300033
[Latos-Grażyński, 1998]	L. Latos-Grażyński, J. Johnson, S. Attar, M.M. Olmstead, A.L. Balch, Reactivity of the verdoheme analogues, 5-oxaporphyrin complexes of cobalt(II) and zinc(II), with nucleophiles: Opening of the planar macrocycle by alkoxide addition to form helical complexes, Inorg. Chem. 37 (1998) 4493–4499. https://doi.org/10.1021/ic971584h
[Leumann, 1984]	C. Leumann, A. Eschenmoser, Chemistry of pyrrocorphins: Methylative opening of the macrocycle between rings A and D, a side reaction in the peripheral C-methylation of a 20-methyl-pyrrocorphinate, J. Chem. Soc., Chem. Commun. (1984) 583–585. https://doi.org/10.1039/c39840000583
[Lord, 2000]	P.A. Lord, M.M. Olmstead, A.L. Balch, Redox characteristics of nickel and palladium complexes of the open-chain tetrapyrrole octaethylbilindione: A biliverdin model, Inorg. Chem. 39 (2000) 1128–1134. https://doi.org/10.1021/ic9910209
[Lord, 2001]	P.A. Lord, B.C. Noll, M.M. Olmstead, A.L. Balch, A remarkable skeletal rearrangement of a coordinated tetrapyrrole: Chemical consequences of palladium π-coordination to a bilindione, J. Am. Chem. Soc. 123 (2001) 10554–10559. https://doi.org/10.1021/ja010647z
[McDonagh, 1982]	A.F. McDonagh, L.A. Palma, D.A. Lightner, Phototherapy for neonatal jaundice. Stereospecific and regioselective photoisomerization of bilirubin bound to human serum albumin and NMR characterization of intramolecularly cyclized photoproducts, J. Am. Chem. Soc. 104 (1982) 6867–6869. https://doi.org/10.1021/ja00388a104
[McDonagh, 1986]	A.F. McDonagh, D.A. Lightner, M. Reisinger, L.A. Palma, Human serum albumin as a chiral template. Stereoselective photocyclization of bilirubin, J. Chem. Soc., Chem. Commun. (1986) 249-250. https://doi.org/10.1039/c39860000249
[McDonagh, 2007]	A.F. McDonagh, D.A. Lightner, Influence of conformation and intramolecular hydrogen bonding on the acyl glucuronidation and biliary excretion of acetylenic bis-dipyrrinones related to bilirubin, J. Med. Chem. 50 (2007) 480–488. https://doi.org/10.1021/jm0609521
[Mizutani, 1998]	T. Mizutani, S. Yagi, A. Honmaru, S. Murakami, M. Furusyo, T. Takagishi, H. Ogoshi, Helical chirality induction in zinc bilindiones by amino acid esters and amines, J. Org. Chem. 63 (1998) 8769–8784. https://doi.org/10.1021/jo980819j
[Mizutani, 2016]	T. Mizutani, Coupled oxidation of iron tetraarylporphyrins as a synthetic tool for linear tetrapyrroles, J. Porphyrins Phthalocyanines 20 (2016) 108–116. https://doi.org/10.1142/S1088424616300044
[Murakami, 1969]	Y. Murakami, Y. Kohno, Y. Matsuda, Transition-metal complexes of pyrrole pigments, II. Cobalt(II) and nickel(II) complexes of 1,19-dideoxy- 8,12-dicarbethoxy-1,3,7,13,17,17-hexamethylbiladiene-ac, Inorg. Chim. Acta 3 (1969) 671–675. https://doi.org/10.1016/S0020-1693(00)92575-1
[Murakami, 1971]	Y. Murakami, Y. Matsuda, Y. Kanaoka, Transition-metal complexes of pyrrole pigments. III. Copper(II) and zinc(II) complexes of 1,19-dideoxy-8,12-dicarbethoxy-1,3,7,13,17,19-hexamethylbiladiene-ac, Bull. Chem. Soc. Jpn. 44 (1971) 409–415. https://doi.org/10.1246/bcsj.44.409
[Murakami, 1973]	Y. Murakami, Y. Matsuda, S.-I. Kobayashi, Transition-metal complexes of pyrrole pigments. Part VII. Cobalt(II) and zinc(II) chelates of some tripyrrene-b and bilene-b ligands, J. Chem. Soc., Dalton Trans. (1973) 1734–1737. https://doi.org/10.1039/dt9730001734
[Mwakwari, 2007]	C. Mwakwari, F.R. Fronczek, K.M. Smith, b-Bilene to a,c-biladiene transformation during syntheses of isoporphyrins and porphyrins, Chem. Commun. (2007) 2258–2260. https://doi.org/10.1039/b705182d
[Nakamura, 1988]	H. Nakamura, B. Musicki, Y. Kishi, O. Shimomura, Structure of the light emitter in krill (Euphausia pacifica) bioluminescence, J. Am. Chem. Soc. 110 (1988) 2683–2685. https://doi.org/10.1021/ja00216a070
[Nakamura, 1989]	H. Nakamura, Y. Kishi, O. Shimomura, D. Morse, J.W. Hastings, Structure of dinoflagellate luciferin and its enzymic and nonenzymic air-oxidation products, J. Am. Chem. Soc. 111 (1989) 7607–7611. https://doi.org/10.1021/ja00201a050
[Nakamura, 2011]	R. Nakamura, K. Kakeya, N. Furuta, E. Muta, H. Nishisaka, T. Mizutani, Synthesis of para- or ortho-substituted triarylbilindiones and tetraarylbiladienones by coupled oxidation of tetraarylporphyrins, J. Org. Chem. 76 (2011) 6108–6115. https://doi.org/10.1021/jo2007994
[Nesvadba, 1987]	P. Nesvadba, A. Gossauer, Synthesis of bile pigments. 14. Synthesis of a bilindionostilbenoparacyclophane as a model for “stretched” bile pigment chromophores of biliproteins, J. Am. Chem. Soc. 109 (1987) 6545–6546. https://doi.org/10.1021/ja00255a069
[Nesvadba, 1994]	P. Nesvadba, D. Ngoc-Phan, F. Nydegger, A.E. Ferao, A. Gossauer, Syntheses of bile pigments. Part 18. Synthesis and conformational studies of oxa- and thia-deaza-biliverdin analogues, Helv. Chim. Acta 77 (1994) 1837–1850. https://doi.org/10.1002/hlca.19940770715
[Nguyen, 2020]	K.C. Nguyen, P. Wang, R.D. Sommer, J.S. Lindsey, Asymmetric synthesis of a bacteriochlorophyll model compound containing trans-dialkyl substituents in ring D, J. Org. Chem. 85 (2020) 6605–6619. https://doi.org/10.1021/acs.joc.0c00608
[Nesvadba, 1994]	P. Nesvadba, D. Ngoc-Phan, F. Nydegger, A.E. Ferao, A. Gossauer, Syntheses of bile pigments. Part 18. Synthesis and conformational studies of oxa- and thia-deaza-biliverdin analogues, Helv. Chim. Acta 77 (1994) 1837–1850. https://doi.org/10.1002/hlca.19940770715
[Ongayi, 2006]	O. Ongayi, M.G.H. Vicente, Z. Ou, K.M. Kadish, M.R. Kumar, F.R. Fronczek, K.M. Smith, Synthesis and electrochemistry of undeca-substituted metallo-benzoylbiliverdins, Inorg. Chem. 45 (2006) 1463–1470. https://doi.org/10.1021/ic050841c
[Paolesse, 2003]	R. Paolesse, A. Froiio, S. Nardis, M. Mastroianni, M. Russo, D.J. Nurco, K.M. Smith, Novel aspects of the chemistry of 1,19-diunsubstituted a,c-biladienes, J. Porphyrins Phthalocyanines 07 (2003) 585–592. https://doi.org/10.1142/S1088424603000744
[Paolesse, 2008]	R. Paolesse, A. Alimelli, A. D'Amico, M. Venanzi, G. Battistini, M. Montalti, D. Filippini, I. Lundström, C. Di Natale, Insights on the chemistry of a,c-biladienes from a CSPT investigation, New J. Chem. 32 (2008) 1162–1166. https://doi.org/10.1039/b800512e
[Pasquier, 1987]	C. Pasquier, A. Gossauer, W. Keller, C. Kratky, Syntheses of bile pigments. Part 15. First unequivocal assignment of the absolute configuration of an urobilinoid bile pigment by X-ray diffraction analysis of its synthetic precursor, Helv. Chim. Acta 70 (1987) 2098–2109. https://doi.org/10.1002/hlca.19870700815
[Pfeiffer, 1994]	W.P. Pfeiffer, D.A. Lightner, Homorubin. A centrally homologated bilirubin, Tetrahedron Lett. 35 (1994) 9673–9676. https://doi.org/10.1016/0040-4039(94)88356-4
[Risch, 1984]	N. Risch, A. Schormann, H. Brockmann, Photobilin e. Photooxidation von bacteriochlorophyll-e-derivaten, Tetrahedron Lett. 25 (1984) 5993–5996. https://doi.org/10.1016/S0040-4039(01)81741-X
[Rumyantsev, 2009]	E.V. Rumyantsev, S.P. Makarova, E.V. Antina, Protonation and solvation effects in the reaction of zinc 1,2,3,7,8,12,13,17,18,19-decamethylbiladien-a,c complex formation, Russ. J. Gen. Chem. 79 (2009) 2420–2424. https://doi.org/10.1134/S1070363209110231
[Savoldelli, 2017]	A. Savoldelli, R. Paolesse, F.R. Fronczek, K.M. Smith, M.G.H. Vicente, BODIPY dyads from a,c-biladiene salts, Org. Biomol. Chem. 15 (2017) 7255–7257. https://doi.org/10.1039/C7OB01797A
[Shimada, 2022]	K. Shimada, T. Mizutani, Synthesis and reactivity of 10,15,20-triaryl-5-oxaporphyrin copper complexes, Tetrahedron Lett. 103 (2022) 153977. https://doi.org/10.1016/j.tetlet.2022.153977
[Shimomura, 1995]	O. Shimomura, The roles of the two highly unstable components F and P involved in the bioluminescence of euphausiid shrimps, J. Biolumin. Chemilumin. 10 (1995) 91–101. https://doi.org/10.1002/bio.1170100205
[Singleton, 1965]	J.W. Singleton, L. Laster, Biliverdin reductase of guinea pig liver, J. Biol. Chem. 240 (1965) 4780–4789. https://doi.org/10.1016/S0021-9258(18)97023-7
[Smith, 1980]	K.M. Smith, S.B. Brown, R.F. Troxler, J.-J. Lai, Mechanism of photo-oxygenation of meso-tetraphenylporphyrin metal complexes, Tetrahedron Lett. 21 (1980) 2763–2766. https://doi.org/10.1016/S0040-4039(00)78600-X
[Smith, 1986]	K.M. Smith, O.M. Minnetian, Cyclizations of 1′,8′-dimethyl-a,c-biladiene salts to give porphyrins: A study with various oxidizing agents, J. Chem. Soc., Perkin Trans. 1 (1986) 277–280. https://doi.org/10.1039/P19860000277
[Suresh, 2009]	M. Suresh, S.K. Mishra, S. Mishra, A. Das, The detection of Hg2+ by cyanobacteria in aqueous media, Chem. Commun. (2009) 2496–2498. https://doi.org/10.1039/b821687h
[Taniguchi, 2018]	M. Taniguchi, J.S. Lindsey, Database of absorption and fluorescence spectra of >300 common compounds for use in PhotochemCAD, Photochem. Photobiol. 94 (2018) 290–327. https://doi.org/10.1111/php.12860
[Terry, 1993]	M.J. Terry, M.D. Maines, J.C. Lagarias, Inactivation of phytochrome- and phycobiliprotein-chromophore precursors by rat liver biliverdin reductase, J. Biol. Chem. 268 (1993) 26099–26106. https://doi.org/10.1016/S0021-9258(19)74286-0
[Tipton, 2001]	A.K. Tipton, D.A. Lightner, A.F. McDonagh, Synthesis and metabolism of the first thia-bilirubin, J. Org. Chem. 66 (2001) 1832–1838. https://doi.org/10.1021/jo001598w
[Tu, 2003]	B.B. Tu, D.A. Lightner, A novel diacetylenic bilirubin, J. Heterocycl. Chem. 40 (2003) 707–712. https://doi.org/10.1002/jhet.5570400424
[Wang, 2020]	P. Wang, F. Lu, J.S. Lindsey, Use of the nascent isocyclic ring to anchor assembly of the full skeleton of model chlorophylls, J. Org. Chem. 85 (2020) 702–715. https://doi.org/10.1021/acs.joc.9b02770
[Weller, 1980]	J. Weller, A. Gossauer, Synthesen von Gallenfarbstoffen, X. Synthese und Photoisomerisierung des racem. Phytochromobilin‐dimethylesters, Chem. Ber. 113 (1980) 1603–1611. https://doi.org/10.1002/cber.19801130439
[Wu, 2003]	C. Wu, H. Akimoto, Y. Ohmiya, Tracer studies on dinoflagellate luciferin with [15N]-glycine and [15N]-L-glutamic acid in the dinoflagellate Pyrocystis lunula, Tetrahedron Lett. 44 (2003) 1263–1266. https://doi.org/10.1016/S0040-4039(02)02815-0
[Yamada, 2022]	K. Yamada, T. Yatabe, K.-S. Yoon, S. Ogo, Cp*Ir complex with mesobiliverdin ligand isolated from Thermoleptolyngbya sp. O-77, J. Organomet. Chem. 964 (2022) 122302. https://doi.org/10.1016/j.jorganchem.2022.122302
[Yamauchi, 2005]	T. Yamauchi, T. Mizutani, K. Wada, S. Horii, H. Furukawa, S. Masaoka, H.-C. Chang, S. Kitagawa, A facile and versatile preparation of bilindiones and biladienones from tetraarylporphyrins, Chem. Commun. (2005) 1311. https://doi.org/10.1039/b414299c
[Yang, 1991]	B. Yang, M.D. Morris, M. Xie, D.A. Lightner, Resonance Raman spectroscopy of bilirubins: Band assignments and application to bilirubin/lipid complexation, Biochemistry 30 (1991) 688–694. https://doi.org/10.1021/bi00217a015
[Zhang, 2017]	S. Zhang, J.S. Lindsey, Construction of the bacteriochlorin macrocycle with concomitant Nazarov cyclization to form the annulated isocyclic ring: Analogues of bacteriochlorophyll a, J. Org. Chem. 82 (2017) 2489–2504. https://doi.org/10.1021/acs.joc.6b02878