Abstract
Most syntheses of meso-substituted porphyrinoid rely on acid-catalyzed condensation of pyrrole segments with aldehyde units followed by oxidation. This standard procedure is convenient but generally is low yielding. However, modern synthetic methodologies would offer an expeditious route to several intriguing porphyrinoids. In particular, the metal template strategy using dipyrrin metal complexes is effective to construct porphyrin-like cyclic π-conjugated systems, which are otherwise difficult to access by the conventional methodology.
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References
Kadish KM, Smith KM, Guilard R(eds) (2010) Handbook of porphyrin science, vol 1–35. World Scientific Publishing, Singapore
Wood TE, Thompson A (2007) Advances in the chemistry of dipyrrins and their complexes. Chem Rev 107(5):1831–1861. doi:10.1021/cr050052c
Loudet A, Burgess K (2007) BODIPY dyes and their derivatives: syntheses and spectroscopic properties. Chem Rev 107(11):4891–4932
Ulrich G, Ziessel R, Harriman A (2008) The chemistry of fluorescent bodipy dyes: versatility unsurpassed. Angew Chem Int Ed 47(7):1184–1201
Ni Y, Wu J (2014) Far-red and near infrared BODIPY dyes: synthesis and applications for fluorescent pH probes and bio-imaging. Org Biomol Chem 12(23):3774–3791. doi:10.1039/C3OB42554A
Lu H, Mack J, Yang Y, Shen Z (2014) Structural modification strategies for the rational design of red/NIR region BODIPYs. Chem Soc Rev 43(13):4778–4823. doi:10.1039/C4CS00030G
Sakida T, Yamaguchi S, Shinokubo H (2011) Metal-mediated synthesis of antiaromatic porphyrinoids from a BODIPY precursor. Angew Chem Int Ed 50(10):2280–2283. doi:10.1002/anie.201006314
Tahara K, Tobe Y (2006) Molecular loops and belts. Chem Rev 106(12):5274–5290. doi:10.1021/cr050556a
Zhang W, Moore JS (2006) Shape-persistent macrocycles: structures and synthetic approaches from arylene and ethynylene building blocks. Angew Chem Int Ed 45(27):4416–4439. doi:10.1002/anie.200503988
Spitler EL, Johnson CA, Haley MM (2006) Renaissance of annulene chemistry. Chem Rev 106(12):5344–5386. doi:10.1021/cr050541c
Wolfe JP, Wagaw S, Marcoux J-F, Buchwald SL (1998) Rational development of practical catalysts for aromatic carbon − nitrogen bond formation. Acc Chem Res 31(12):805–818. doi:10.1021/ar9600650
Hartwig JF (1998) Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: scope and mechanism. Angew Chem Int Ed 37(15):2046–2067
Hartwig JF (2008) Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides. Acc Chem Res 41(11):1534–1544. doi:10.1021/ar800098p
Surry DS, Buchwald SL (2008) Biaryl phosphane ligands in palladium-catalyzed amination. Angew Chem Int Ed 47(34):6338–6361. doi:10.1002/anie.200800497
Johnson AW, Kay IT, Rodrigo R (1963) 2,2′-bipyrrolic macrocyclic ring systems. J Chem Soc 2336–2342. doi:10.1039/JR9630002336
Horie M, Hayashi Y, Yamaguchi S, Shinokubo H (2012) Synthesis of nickel(II) azacorroles by Pd-catalyzed amination of α,α′-dichlorodipyrrin NiII complex and their properties. Chem Eur J 18(19):5919–5923. doi:10.1002/chem.201200485
Matano Y, Shibano T, Nakano H, Imahori H (2012) Nickel(II) and copper(II) complexes of beta-unsubstituted 5,15-diazaporphyrins and pyridazine-fused diazacorrinoids: metal-template syntheses and peripheral functionalizations. Chem Eur J 18(20):6208–6216. doi:10.1002/chem.201200463
Matano Y, Shibano T, Nakano H, Kimura Y, Imahori H (2012) Free base and metal complexes of 5,15-diaza-10,20-dimesitylporphyrins: synthesis, structures, optical and electrochemical properties, and aromaticities. Inorg Chem 51(23):12879–12890. doi:10.1021/ic301835c
Kamiya H, Kondo T, Sakida T, Yamaguchi S, Shinokubo H (2012) meso-thiaporphyrinoids revisited: missing of sulfur by small metals. Chem Eur J 18(50):16129–16135. doi:10.1002/chem.201203255
Sakow D, Böker B, Brandhorst K, Burghaus O, Bröring M (2013) 10-heterocorroles: ring-contracted porphyrinoids with fine-tuned aromatic and metal-binding properties. Angew Chem Int Ed 52(18):4912–4915. doi:10.1002/anie.201300757
Broadhurst MJ, Grigg R, Johnson AW (1970) Preparation of some sulphur-containing polypyrrolic macrocycles – sulphur extrusion from a meso-thiaphlorin. J Chem Soc D 13:807–809. doi:10.1039/c29700000807
Broadhurst MJ, Grigg R, Johnson AW (1972) Sulfur extrusion reactions applied to synthesis of corroles and related systems. J Chem Soc Perkin Trans 1(9–10):1124–1135. doi:10.1039/p19720001124
Wachi N, Kondo T, Ito S, Hiroto S, Shin J-Y, Shinokubo H (2014) Synthesis, reactivity, and property of 5,15-dithiaporphyrin copper(II) complex. J Porphyrins Phthalocyanines 18(8–9):675–678
Bröring M, Köhler S, Kleeberg C (2008) Norcorrole: observation of the smallest porphyrin variant with a N4 core. Angew Chem Int Ed 47(30):5658–5660. doi:10.1002/anie.200801196
Ito T, Hayashi Y, Shimizu S, Shin J-Y, Kobayashi N, Shinokubo H (2012) Gram-scale synthesis of Nickel(II) norcorrole: the smallest antiaromatic porphyrinoid. Angew Chem Int Ed 51(34):8542–8545. doi:10.1002/anie.201204395
Broring M, Brégier F, Cónsul Tejero E, Hell C, Holthausen MC (2007) Revisiting the electronic ground state of copper corroles. Angew Chem Int Ed 46(3):445–448. doi:10.1002/anie.200603676
Kira M, Ishida S, Iwamoto T, Kabuto C (1999) The first isolable dialkylsilylene. J Am Chem Soc 121(4–1):9722–9723. doi:10.1021/ja9925305
Kira M, Iwamoto T, Ishida S (2007) A helmeted dialkylsilylene. Bull Chem Soc Jpn 80(2):258–275. doi:10.1246/bcsj.80.258
Kira M (2010) An isolable dialkylsilylene and its derivatives. A step toward comprehension of heavy unsaturated bonds. Chem Commun 46(17):2893–2903. doi:10.1039/C002806A
Fukuoka T, Uchida K, Sung YM, Shin J-Y, Ishida S, Lim JM, Hiroto S, Furukawa K, Kim D, Iwamoto T, Shinokubo H (2014) Near-IR absorbing nickel(II) porphyrinoids prepared by regioselective insertion of silylenes into antiaromatic nickel(II) norcorrole. Angew Chem Int Ed 53(6):1506–1509. doi:10.1002/anie.201309921
Kido H, Shin J-Y, Shinokubo H (2013) Selective synthesis of a [32]octaphyrin(1.0.1.0.1.0.1.0) bis(palladium) complex by a metal-templated strategy. Angew Chem Int Ed 52(51):13727–13730. doi:10.1002/anie.201306905
Shin J-Y, Yamada T, Yoshikawa H, Awaga K, Shinokubo H (2014) An antiaromatic electrode-active material enabling high capacity and stable performance of rechargeable batteries. Angew Chem Int Ed 53(12):3096–3101. doi:10.1002/anie.201310374
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Shinokubo, H. (2015). Synthesis of Novel Porphyrinoids from Dipyrrins. In: Akasaka, T., Osuka, A., Fukuzumi, S., Kandori, H., Aso, Y. (eds) Chemical Science of π-Electron Systems. Springer, Tokyo. https://doi.org/10.1007/978-4-431-55357-1_14
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DOI: https://doi.org/10.1007/978-4-431-55357-1_14
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