Synthesis and functionalization of electron-deficient perfluoroalkyl porphyrin building blocks for supermolecular systems

Liu, Rui; Zhu, Jiaqi; Rawson, Jeff; Pederson, Lindsay R.; Cinnater, Victoria L.; Mansergh, Jarrett P.; Therien, Michael J.

doi:10.1142/s1088424623500451

Synthesis and functionalization of electron-deficient perfluoroalkyl porphyrin building blocks for supermolecular systems

Journal Article · Mon Apr 17 00:00:00 EDT 2023 · Journal of Porphyrins and Phthalocyanines

DOI:https://doi.org/10.1142/s1088424623500451· OSTI ID:2419610

Liu, Rui ^[1]; Zhu, Jiaqi ^[2]; Rawson, Jeff ^[2]; Pederson, Lindsay R. ^[2]; Cinnater, Victoria L. ^[2]; Mansergh, Jarrett P. ^[2]; Therien, Michael J. ^[2]

Department of Chemistry, French Family Science Center, 124 Science Drive, Duke University, Durham, NC 27708-0346, USA; OSTI
Department of Chemistry, French Family Science Center, 124 Science Drive, Duke University, Durham, NC 27708-0346, USA

Synthetic strategies for electron-deficient meso-perfluoroalkylporphyrins bearing diverse functional groups are described. Scalable and efficient syntheses for 5-triisopropylsilylethynyl-10,15,20-tris(heptafluoropropyl)porphyrin and 5-triisopropylsilylethynyl-10,20-bis(heptafluoropropyl)porphyrin that equip meso-ethynyl functional groups via the bilane route have been established, along with a refined route to [5,15-bis(heptafluoropropyl)porphinato]zinc(II). meso-Position halogenation of [5,15-bis(heptafluoropropyl)porphinato]zinc(II) was achieved by selective meso-nitration and subsequent reduction, diazonium salt formation, and iodination reactions. Computational data describe the low energy excited states of these chromophores and the electronic structural factors that control reactivity of these meso-perfluoroalkyl substituted porphyrin complexes. meso-Functionalized [5-triisopropylsilylethynyl-10,20-bis(heptafluoropropyl)porphinato]zinc(II) and [5-iodo-10,20-bis(heptafluoropropyl)porphinato]zinc(II) building blocks lay the foundation for the construction of highly conjugated multiporphyrin arrays that feature electronic structural properties important for the development of n-type materials and high potential photooxidants.

Research Organization:: Duke Univ., Durham, NC (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0001517

OSTI ID:: 2419610

Journal Information:: Journal of Porphyrins and Phthalocyanines, Journal Name: Journal of Porphyrins and Phthalocyanines Journal Issue: 05 Vol. 27; ISSN 1088-4246

Publisher:: World Scientific

Country of Publication:: United States

Language:: English

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Synthesis, structure, electronic spectroscopy, photophysics, electrochemistry, and X-ray photoelectron spectroscopy of highly-electron-deficient [5,10,15,20-tetrakis(perfluoroalkyl)porphinato]zinc(II ) complexes and their free base derivatives

Journal Article · Wed Sep 04 00:00:00 EDT 1996 · Journal of the American Chemical Society · OSTI ID:380902

Exceptional electronic modulation of porphyrins through meso-arylethynyl groups. Electronic spectroscopy, electronic structure, and electrochemistry of [5,15-bis[(aryl)ethynyl]-10,20-diphenylporphinato]zinc(II) complexes. X-ray crystal structures of [5,15-bis[(4`-fluorophenyl)ethynyl]-10,20-diphenylp orphinato]zinc(II) and 5,15-bis [(4`-methoxyphenyl)ethynyl]-10,20-diphenylporphyrin

Journal Article · Tue Nov 26 23:00:00 EST 1996 · Journal of the American Chemical Society · OSTI ID:437399

Boosting Photoelectric Conductivity in Porphyrin-Based MOFs Incorporating C₆₀

Journal Article · Wed Jan 22 23:00:00 EST 2020 · Journal of Physical Chemistry. C · OSTI ID:1714366

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Synthesis and functionalization of electron-deficient perfluoroalkyl porphyrin building blocks for supermolecular systems

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