Panchromatic π-Extended Porphyrins from Conjugation with Quinones - PubMed (original) (raw)
. 2016 May;81(5):477-488.
doi: 10.1002/cplu.201600115. Epub 2016 Apr 6.
Affiliations
- PMID: 31968777
- DOI: 10.1002/cplu.201600115
Panchromatic π-Extended Porphyrins from Conjugation with Quinones
Srinivas Banala et al. Chempluschem. 2016 May.
Abstract
Typical porphyrins are coloured compounds due to their characteristic wavelength-selective visible light absorptions. An exceptional "blackened" ZnII -porphyrin was recently obtained from fusing the β,β'-positions of the porphyrin core with four quinone units. Here, studies with metal-free and NiII -containing analogues are reported. These quinone-fused porphyrins were prepared from the corresponding β,β'-tetrasulfolenoporphyrins via thermally generated porphyrindienes, which were trapped by [4+2] cycloaddition as benzoquinone cycloadducts, which were subsequently oxidised. By using this strategy, metal-free and NiII -containing porphyrins with one, two, three or four conjugated naphthoquinone moieties were prepared efficiently. The presence of the π-conjugated naphthoquinone moieties changed the porphyrin chromophores profoundly, giving broadly absorbing "blackened" pigments. The influence of coordinated NiII ions, or of the absence of a metal ion in the modified porphyrin core, on their structural and spectroscopic properties was explored. Blackened quinone-conjugated porphyrins might be pigments suitable for solar energy conversion. With their unique peripheral functional groups they are also a set of porphyrins "programmed" for further covalent extension. Thus, they are building blocks for the preparation of supra-porphyrinoid assemblies that might be useful in optoelectronics and in the nanosciences.
Keywords: cycloaddition; naphthoquinones; porphyrinoids; solar energy; transition metals.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Similar articles
- The Breaking and Mending of meso-Tetraarylporphyrins: Transmuting the Pyrrolic Building Blocks.
Brückner C. Brückner C. Acc Chem Res. 2016 Jun 21;49(6):1080-92. doi: 10.1021/acs.accounts.6b00043. Epub 2016 Mar 11. Acc Chem Res. 2016. PMID: 26967793 - Electrochemistry and spectroelectrochemistry of beta,beta'-fused quinoxalinoporphyrins and related extended bis-porphyrins with Co(III), Co(II), and Co(I) central metal ions.
Zhu W, Sintic M, Ou Z, Sintic PJ, McDonald JA, Brotherhood PR, Crossley MJ, Kadish KM. Zhu W, et al. Inorg Chem. 2010 Feb 1;49(3):1027-38. doi: 10.1021/ic901851u. Inorg Chem. 2010. PMID: 20028095 - Near-Infrared-Absorbing Metal-Free Organic, Porphyrin, and Phthalocyanine Sensitizers for Panchromatic Dye-Sensitized Solar Cells.
Brogdon P, Cheema H, Delcamp JH. Brogdon P, et al. ChemSusChem. 2018 Jan 10;11(1):86-103. doi: 10.1002/cssc.201701441. Epub 2017 Dec 20. ChemSusChem. 2018. PMID: 28926685 Review. - Heteroatom-Containing Porphyrin Analogues.
Chatterjee T, Shetti VS, Sharma R, Ravikanth M. Chatterjee T, et al. Chem Rev. 2017 Feb 22;117(4):3254-3328. doi: 10.1021/acs.chemrev.6b00496. Epub 2016 Nov 4. Chem Rev. 2017. PMID: 27813402 Review.
Cited by
- Optical Oxygen Sensors Show Reversible Cross-Talk and/or Degradation in the Presence of Nitrogen Dioxide.
Dalfen I, Pol A, Borisov SM. Dalfen I, et al. ACS Sens. 2022 Oct 28;7(10):3057-3066. doi: 10.1021/acssensors.2c01385. Epub 2022 Sep 15. ACS Sens. 2022. PMID: 36109879 Free PMC article. - Molecular flattening effect to enhance the conductivity of fused porphyrin tape thin films.
Bengasi G, Desport JS, Baba K, Cosas Fernandes JP, De Castro O, Heinze K, Boscher ND. Bengasi G, et al. RSC Adv. 2020 Feb 17;10(12):7048-7057. doi: 10.1039/c9ra09711b. eCollection 2020 Feb 13. RSC Adv. 2020. PMID: 35493879 Free PMC article. - Photoacoustic Imaging Probes Based on Tetrapyrroles and Related Compounds.
Merkes JM, Zhu L, Bahukhandi SB, Rueping M, Kiessling F, Banala S. Merkes JM, et al. Int J Mol Sci. 2020 Apr 27;21(9):3082. doi: 10.3390/ijms21093082. Int J Mol Sci. 2020. PMID: 32349297 Free PMC article. Review. - Quinone-fused porphyrins as contrast agents for photoacoustic imaging.
Banala S, Fokong S, Brand C, Andreou C, Kräutler B, Rueping M, Kiessling F. Banala S, et al. Chem Sci. 2017 Sep 1;8(9):6176-6181. doi: 10.1039/c7sc01369h. Epub 2017 Jun 27. Chem Sci. 2017. PMID: 28989649 Free PMC article. - Furan- and Thiophene-Based Auxochromes Red-shift Chlorin Absorptions and Enable Oxidative Chlorin Polymerizations.
Xiong R, Bornhof AB, Arkhypchuk AI, Orthaber A, Borbas KE. Xiong R, et al. Chemistry. 2017 Mar 23;23(17):4089-4095. doi: 10.1002/chem.201604655. Epub 2017 Jan 23. Chemistry. 2017. PMID: 27859811 Free PMC article.
References
- None
- A. R. Battersby, Science 1994, 264, 1551-1557;
- Handbook of Porphyrin Science, Vol. 1-30 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), World Scientific Publ. Co., Singapore, 2010.
- None
- H. Fischer, K. Zeile, Justus Liebigs Ann. Chem. 1929, 468, 98-116;
LinkOut - more resources
Full Text Sources
Research Materials
Miscellaneous