Porphyrinoid f-Element Complexes

Brewster, James T.; Zafar, Hadiqa; Root, Harrison D.; Thiabaud, Gregory D.; Sessler, Jonathan L.

doi:10.1021/acs.inorgchem.9b00884

Title: Porphyrinoid f-Element Complexes

Journal Article · Mon Jun 17 00:00:00 EDT 2019 · Inorganic Chemistry

DOI:https://doi.org/10.1021/acs.inorgchem.9b00884· OSTI ID:1615761

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Univ. of Texas, Austin, TX (United States)

Porphyrin and related pyrrole-containing macrocycles, collectively porphyrinoids, are adaptable ligands that allow access to a multitude of coordination modes. Judicious modification of the porphyrin core, as well as the pendant substituents, have extended the coordination chemistry of porphyrinoids to include systems that are able to stabilize f-block element complexes with possible utility. Our review focus-es on our group’s efforts to prepare expanded porphyrin and porphyrinogen ligands that can serve as tools to study and apply f-element metal coordination chemistry; it covers the background of the topic, selected syntheses, and application of these species in the chemical and medical sciences

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Research Organization:: Univ. of Texas, Austin, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); Robert A. Welch Foundation

Grant/Contract Number:: FG02-01ER15186; CHE-1807152

OSTI ID:: 1615761

Journal Information:: Inorganic Chemistry, Vol. 59, Issue 1; ISSN 0020-1669

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 15 works

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Acid-triggered release of doxorubicin from a hydrazone-linked Gd ³⁺ -texaphyrin conjugate Lee, Min Hee; Kim, Eun-Joong; Lee, Hyunseung Chemical Communications, Vol. 52, Issue 69 https://doi.org/10.1039/C6CC05673C	journal	January 2016
Gadolinium texaphyrin (Gd-Tex)-malonato-platinum conjugates: Synthesis and comparison with carboplatin in normal and Pt-resistant cell lines Arambula, Jonathan F.; Sessler, Jonathan L.; Fountain, Mark E. Dalton Transactions, Issue 48 https://doi.org/10.1039/b912089k	journal	January 2009
Overcoming biochemical pharmacologic mechanisms of platinum resistance with a texaphyrin–platinum conjugate Arambula, Jonathan F.; Sessler, Jonathan L.; Siddik, Zahid H. Bioorganic & Medicinal Chemistry Letters, Vol. 21, Issue 6 https://doi.org/10.1016/j.bmcl.2011.01.092	journal	March 2011
Texaphyrins: Tumor Localizing Redox Active Expanded Porphyrins F. Arambula, Jonathan; Preihs, Christian; Borthwick, Derric Anti-Cancer Agents in Medicinal Chemistry, Vol. 11, Issue 2 https://doi.org/10.2174/187152011795255894	journal	February 2011
Photoinduced Reduction of Pt ^IV within an Anti-Proliferative Pt ^IV -Texaphyrin Conjugate Thiabaud, Grégory; Arambula, Jonathan F.; Siddik, Zahid H. Chemistry - A European Journal https://doi.org/10.1002/chem.201403559	journal	June 2014
Activation of Platinum(IV) Prodrugs By Motexafin Gadolinium as a Redox Mediator Thiabaud, Gregory; McCall, Rebecca; He, Guangan Angewandte Chemie International Edition, Vol. 55, Issue 41 https://doi.org/10.1002/anie.201604236	journal	July 2016
Near-Infrared Emission of Lanthanide(III) Texaphyrin Complexes Lv, Tian; Sun, Wenfang Journal of Inorganic and Organometallic Polymers and Materials, Vol. 23, Issue 1 https://doi.org/10.1007/s10904-012-9753-1	journal	September 2012
DFT Study of the Active Site of the XoxF-Type Natural, Cerium-Dependent Methanol Dehydrogenase Enzyme Bogart, Justin A.; Lewis, Andrew J.; Schelter, Eric J. Chemistry - A European Journal, Vol. 21, Issue 4 https://doi.org/10.1002/chem.201405159	journal	November 2014
Functional Synthetic Model for the Lanthanide-Dependent Quinoid Alcohol Dehydrogenase Active Site McSkimming, Alex; Cheisson, Thibault; Carroll, Patrick J. Journal of the American Chemical Society, Vol. 140, Issue 4 https://doi.org/10.1021/jacs.7b12318	journal	January 2018
Lanthanide Texaphyrins as Photocatalysts Lammer, Aaron D.; Thiabaud, Grégory; Brewster, James T. Inorganic Chemistry, Vol. 57, Issue 6 https://doi.org/10.1021/acs.inorgchem.8b00248	journal	March 2018
Density Functional Theory Studies of Actinide(III) Motexafins (An-Motex ²⁺ , An = Ac, Cm, Lr). Structure, Stability, and Comparison with Lanthanide(III) Motexafins Cao, Xiaoyan; Li, Quansong; Moritz, Anna Inorganic Chemistry, Vol. 45, Issue 8 https://doi.org/10.1021/ic052128t	journal	April 2006
A Nonaromatic Expanded Porphyrin Derived from Anthracene—A Macrocycle which Unexpectedly Binds Anions Sessler, Jonathan L.; Mody, Tarak D.; Ford, Debra A. Angewandte Chemie International Edition in English, Vol. 31, Issue 4 https://doi.org/10.1002/anie.199204521	journal	April 1992
Schiff-base porphyrin and expanded porphyrin analogs Callaway, Wyeth B.; Veauthier, Jacqueline M.; Sessler, Jonathan L. Journal of Porphyrins and Phthalocyanines, Vol. 08, Issue 01 https://doi.org/10.1142/S1088424604000027	journal	January 2004
Synthesis and Structural Characterization of the First Schiff-Base Macrocycles Containing Terpyrrole Subunits Meyer, Sylvie; Andrioletti, Bruno; Sessler, Jonathan L. The Journal of Organic Chemistry, Vol. 63, Issue 19 https://doi.org/10.1021/jo980628g	journal	September 1998
Calix[4]pyrrole Schiff Base Macrocycles. Novel Binucleating Ligands for μ-Oxo Iron Complexes Veauthier, Jacqueline M.; Cho, Won-Seob; Lynch, Vincent M. Inorganic Chemistry, Vol. 43, Issue 4 https://doi.org/10.1021/ic0352001	journal	February 2004
Calix[4]pyrrole Schiff Base Macrocycles: Novel Binucleating Ligands for Cu(I) and Cu(II) Veauthier, Jacqueline M.; Tomat, Elisa; Lynch, Vincent M. Inorganic Chemistry, Vol. 44, Issue 19 https://doi.org/10.1021/ic050690d	journal	September 2005
Synthesis and Anion Binding Properties of 2,5-Diamidothiophene Polypyrrole Schiff Base Macrocycles Sessler, Jonathan L.; Roznyatovskiy, Vladimir; Pantos, G. Dan Organic Letters, Vol. 7, Issue 23 https://doi.org/10.1021/ol052162b	journal	November 2005
Binuclear Fluoro-Bridged Zinc and Cadmium Complexes of a Schiff Base Expanded Porphyrin: Fluoride Abstraction from the Tetrafluoroborate Anion Tomat, Elisa; Cuesta, Luciano; Lynch, Vincent M. Inorganic Chemistry, Vol. 46, Issue 16 https://doi.org/10.1021/ic700933p	journal	August 2007
The template synthesis and X-ray characterization of pyrrole-derived hexadentate uranyl(VI) Schiff-base macrocyclic complexes Sessler, Jonathan L.; Mody, Tarak D.; Dulay, Maria T. Inorganica Chimica Acta, Vol. 246, Issue 1-2 https://doi.org/10.1016/0020-1693(96)05046-3	journal	May 1996
Characterization of the interactions between neptunyl and plutonyl cations and expanded porphyrins Sessler, Jonathan L.; Gorden, Anne E. V.; Seidel, Daniel Inorganica Chimica Acta, Vol. 341 https://doi.org/10.1016/S0020-1693(02)01202-1	journal	December 2002
Synthesis and Characterization of New Non-aromatic Texaphyrin-type Expanded Porphyrins Meyer, Sylvie; Hoehner, Michael C.; Lynch, Vincent Journal of Porphyrins and Phthalocyanines, Vol. 03, Issue 02 https://doi.org/10.1002/(SICI)1099-1409(199902)3:2<148::AID-JPP111>3.0.CO;2-O	journal	February 1999
Schiff base oligopyrrolic macrocycles as ligands for lanthanides and actinides Sessler, Jonathan L.; Melfi, Patricia J.; Tomat, Elisa Journal of Alloys and Compounds, Vol. 418, Issue 1-2 https://doi.org/10.1016/j.jallcom.2005.06.089	journal	July 2006
Sulphur extrusion reactions applied to the synthesis of corroles and related systems Broadhurst, M. J.; Grigg, R.; Johnson, A. W. Journal of the Chemical Society, Perkin Transactions 1 https://doi.org/10.1039/p19720001124	journal	January 1972
Synthetic and structural studies of sapphyrin, a 22-.pi.-electron pentapyrrolic "expanded porphyrin" Sessler, Jonathan L.; Cyr, Michael J.; Lynch, Vincent Journal of the American Chemical Society, Vol. 112, Issue 7 https://doi.org/10.1021/ja00163a059	journal	March 1990
The photoexcited triplet state of sapphyrin dication. Unusual spin alignment in monomers and spin delocalization in dimers Levanon, Haim; Regev, Ayelet; Michaeli, Shalom Chemical Physics Letters, Vol. 174, Issue 3-4 https://doi.org/10.1016/0009-2614(90)85338-D	journal	November 1990
Photodynamic inactivation of enveloped viruses using sapphyrin, a 22 pi-electron expanded porphyrin: possible approaches to prophylactic blood purification protocols Sessler, Jonathan L.; Cyr, Michael J.; Maiya, Bhaskar G. OE/LASE '90, 14-19 Jan., Los Angeles, CA, SPIE Proceedings https://doi.org/10.1117/12.17669	conference	July 1990
In vitro photodynamic activity of diprotonated sapphyrin: a 22-.pi.-electron pentapyrrolic porphyrin-like macrocycle Maiya, Bhaskar G.; Cyr, Mike.; Harriman, Anthony. The Journal of Physical Chemistry, Vol. 94, Issue 9 https://doi.org/10.1021/j100372a043	journal	May 1990
Phosphate anion binding: enhanced transport of nucleotide monophosphates using a sapphyrin carrier Furuta, Hiroyuki; Cyr, Michael J.; Sessler, Jonathan L. Journal of the American Chemical Society, Vol. 113, Issue 17 https://doi.org/10.1021/ja00017a051	journal	August 1991
Enhanced transport of fluoride anion effected using protonated sapphyrin as a carrier Sessler, Jonathan L.; Ford, Debra A.; Cyr, Michael J. Journal of the Chemical Society, Chemical Communications, Issue 24 https://doi.org/10.1039/c39910001733	journal	January 1991
Diprotonated sapphyrin: a fluoride selective halide anion receptor Shionoya, Mitsuhiko; Furuta, Hiroyuki; Lynch, Vincent Journal of the American Chemical Society, Vol. 114, Issue 14 https://doi.org/10.1021/ja00040a034	journal	July 1992
Metal Carbonyl Complexes of Sapphyrins Burrell, Anthony K.; Sessler, Jonathan L.; Cyr, Michael J. Angewandte Chemie International Edition in English, Vol. 30, Issue 1 https://doi.org/10.1002/anie.199100911	journal	January 1991
Synthesis and x-ray Structure of Selenasapphyrin Lisowski, Jerzy; Sessler, Jonathan L.; Lynch, Vincent Inorganic Chemistry, Vol. 34, Issue 13 https://doi.org/10.1021/ic00117a032	journal	June 1995
Sapphyrins and heterosapphyrins. Sessler, Jonathan L.; Cyr, Mike; Burrell, Anthony K. Tetrahedron, Vol. 48, Issue 44 https://doi.org/10.1016/S0040-4020(01)81183-2	journal	January 1992
Nucleophilic attack at the meso position of a uranyl sapphyrin complex Burrell, Anthony K.; Cyr, Michael J.; Lynch, Vincent Journal of the Chemical Society, Chemical Communications, Issue 24 https://doi.org/10.1039/c39910001710	journal	January 1991
Synthesis and characterization of an oxasapphyrin-uranyl complex Sessler, Jonathan L.; Gebauer, Andreas Chemical Communications, Issue 17 https://doi.org/10.1039/a803975e	journal	January 1998
Synthesis and characterization of quinone-substituted octaalkyl porphyrin monomers and dimers Sessler, Jonathan L.; Johnson, Martin R.; Creager, Stephen E. Journal of the American Chemical Society, Vol. 112, Issue 25 https://doi.org/10.1021/ja00181a038	journal	December 1990
Uranylpentaphyrin: an actinide complex of an expanded porphyrin Burrell, Anthony K.; Hemmi, Gregory; Lynch, Vincent Journal of the American Chemical Society, Vol. 113, Issue 12 https://doi.org/10.1021/ja00012a053	journal	June 1991
2,2':5',2″-Terpyrrole ^1a Rapoport, Henry; Castagnoli, Neal; Holden, Kenneth G. The Journal of Organic Chemistry, Vol. 29, Issue 4 https://doi.org/10.1021/jo01027a029	journal	April 1964
A general synthetic route to 2,2':5',2''-terpyrrole, 2,5-di(2-pyrryl)thiophene, and alkyl-substituted analogs Merrill, Bryon A.; LeGoff, Eugene The Journal of Organic Chemistry, Vol. 55, Issue 9 https://doi.org/10.1021/jo00296a062	journal	April 1990
Well-Defined Oligo(pyrrole-2,5-diyl)s by the Ullmann Reaction Groenendaal, L.; Peerlings, H. W. I.; van Dongen, J. L. J. Macromolecules, Vol. 28, Issue 1 https://doi.org/10.1021/ma00105a015	journal	January 1995
Hexaalkyl Terpyrrole: A New Building Block for the Preparation of Expanded Porphyrins Sessler, Jonathan L.; Weghorn, Steven J.; Hiseada, Yoshio Chemistry - A European Journal, Vol. 1, Issue 1 https://doi.org/10.1002/chem.19950010110	journal	April 1995
Synthesis and characterization of an amethyrin-uranyl complex displaying aromatic character Brewster, James T.; Aguilar, Apolonio; Anguera, Gonzalo Journal of Coordination Chemistry, Vol. 71, Issue 11-13 https://doi.org/10.1080/00958972.2018.1458230	journal	April 2018
Hexaphyrin(1.0.1.0.0.0): An Expanded Porphyrin Ligand for the Actinide Cations Uranyl (UO22+) and Neptunyl (NpO2+) Sessler, Jonathan L.; Seidel, Daniel; Vivian, Anne E. Angewandte Chemie International Edition, Vol. 40, Issue 3 https://doi.org/10.1002/1521-3773(20010202)40:3<591::AID-ANIE591>3.0.CO;2-0	journal	January 2001
Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO ₂ ²⁺ ) Cation Anguera, Gonzalo; Brewster, James T.; Moore, Matthew D. Inorganic Chemistry, Vol. 56, Issue 16 https://doi.org/10.1021/acs.inorgchem.7b01668	journal	July 2017
Synthesis and Characterization of a Binuclear Copper(II) Naphthoisoamethyrin Complex Displaying Weak Antiferromagnetic Coupling Brewster, James T.; Anguera, Gonzalo; Moore, Matthew D. Inorganic Chemistry, Vol. 56, Issue 21 https://doi.org/10.1021/acs.inorgchem.7b01669	journal	October 2017
Hexaphyrin(1.0.1.0.0.0). A new colorimetric actinide sensor Sessler, Jonathan L.; Melfi, Patricia J.; Seidel, Daniel Tetrahedron, Vol. 60, Issue 49 https://doi.org/10.1016/j.tet.2004.08.055	journal	November 2004
Immobilization of a hexaphyrin(1.0.1.0.0.0) derivative onto a tentagel-amino resin and its use in uranyl cation detection Melfi, Patricia J.; Camiolo, Salvatore; Lee, Jeong Tae Dalton Transactions, Issue 12 https://doi.org/10.1039/b718627d	journal	January 2008
Synthesis and characterization of a dipyriamethyrin–uranyl complex Brewster, James T.; He, Qing; Anguera, Gonzalo Chemical Communications, Vol. 53, Issue 36 https://doi.org/10.1039/C7CC01674C	journal	January 2017
UO ₂ ²⁺ -mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex Brewster, James T.; Root, Harrison D.; Mangel, Daniel Chemical Science, Vol. 10, Issue 21 https://doi.org/10.1039/C9SC01593K	journal	January 2019
Cyclo[8]pyrrole: A Simple-to-Make Expanded Porphyrin with No Meso Bridges Seidel, Daniel; Lynch, Vincent; Sessler, Jonathan L. Angewandte Chemie International Edition, Vol. 41, Issue 8 https://doi.org/10.1002/1521-3773(20020415)41:8<1422::AID-ANIE1422>3.0.CO;2-O	journal	April 2002
Formation and Properties of Cyclo[6]pyrrole and Cyclo[7]pyrrole Köhler, Thomas; Seidel, Daniel; Lynch, Vincent Journal of the American Chemical Society, Vol. 125, Issue 23 https://doi.org/10.1021/ja035089y	journal	June 2003
Redox Behavior of Cyclo[6]pyrrole in the Formation of a Uranyl Complex Melfi, Patricia J.; Kim, Sung Kuk; Lee, Jeong Tae Inorganic Chemistry, Vol. 46, Issue 13 https://doi.org/10.1021/ic700781t	journal	June 2007
Cyclo[ m ]pyridine[ n ]pyrroles: Hybrid Macrocycles That Display Expanded π-Conjugation upon Protonation Zhang, Zhan; Lim, Jong Min; Ishida, Masatoshi Journal of the American Chemical Society, Vol. 134, Issue 9 https://doi.org/10.1021/ja211985k	journal	February 2012
18[Hexa(2,6)pyridinocoronand-6]: "Sexipyridine" Newkome, George R.; Lee, H. W. Journal of the American Chemical Society, Vol. 105, Issue 18 https://doi.org/10.1021/ja00356a061	journal	September 1983
Cyclosexipyridines Toner, John L. Tetrahedron Letters, Vol. 24, Issue 27 https://doi.org/10.1016/S0040-4039(00)88001-6	journal	January 1983
Torands: rigid toroidal macrocycles. Calcium sequestration by a member of this new ligand class Bell, Thomas W.; Firestone, Albert. Journal of the American Chemical Society, Vol. 108, Issue 25 https://doi.org/10.1021/ja00285a049	journal	December 1986
A Hybrid Macrocycle with a Pyridine Subunit Displays Aromatic Character upon Uranyl Cation Complexation Ho, I-Ting; Zhang, Zhan; Ishida, Masatoshi Journal of the American Chemical Society, Vol. 136, Issue 11 https://doi.org/10.1021/ja412520g	journal	March 2014
Calix[4]pyrroles: Old Yet New Anion-Binding Agents Gale, Philip A.; Sessler, Jonathan L.; Král, Vladimír Journal of the American Chemical Society, Vol. 118, Issue 21 https://doi.org/10.1021/ja960307r	journal	January 1996
Ueber ein Condensationsproduct von Pyrrol mit Aceton Baeyer, Adolf Berichte der deutschen chemischen Gesellschaft, Vol. 19, Issue 2 https://doi.org/10.1002/cber.188601902121	journal	July 1886
Calixpyrroles Gale, Philip A.; Sessler, Jonathan L.; Král, Vladimír Chemical Communications, Issue 1 https://doi.org/10.1039/a706280j	journal	January 1998
Recent Advancements in Calix[4]pyrrole-Based Anion-Receptor Chemistry: Calix[4]pyrrole-Based Anion Receptor Chemistry Saha, Indrajit; Lee, Jeong Tae; Lee, Chang-Hee European Journal of Organic Chemistry, Vol. 2015, Issue 18 https://doi.org/10.1002/ejoc.201403701	journal	March 2015
Calix[4]pyrroles: versatile molecular containers with ion transport, recognition, and molecular switching functions Kim, Dong Sub; Sessler, Jonathan L. Chemical Society Reviews, Vol. 44, Issue 2 https://doi.org/10.1039/C4CS00157E	journal	January 2015
Calix[4]pyrrole-Based Ion Pair Receptors Kim, Sung Kuk; Sessler, Jonathan L. Accounts of Chemical Research, Vol. 47, Issue 8 https://doi.org/10.1021/ar500157a	journal	June 2014
Tetrathiafulvalene-calix[4]pyrrole: a versatile synthetic receptor for electron-deficient planar and spherical guests Bähring, Steffen; Root, Harrison D.; Sessler, Jonathan L. Organic & Biomolecular Chemistry, Vol. 17, Issue 10 https://doi.org/10.1039/C8OB02514B	journal	January 2019
Macrocycle-based metal-organic frameworks Zhang, Huacheng; Zou, Ruqiang; Zhao, Yanli Coordination Chemistry Reviews, Vol. 292 https://doi.org/10.1016/j.ccr.2015.02.012	journal	May 2015
Switchable π-coordination and C–H metallation in small-cavity macrocyclic uranium and thorium complexes Arnold, Polly L.; Farnaby, Joy H.; White, Rebecca C. Chem. Sci., Vol. 5, Issue 2 https://doi.org/10.1039/C3SC52072B	journal	January 2014
Organometallic neptunium(III) complexes Dutkiewicz, Michał S.; Farnaby, Joy H.; Apostolidis, Christos Nature Chemistry, Vol. 8, Issue 8 https://doi.org/10.1038/nchem.2520	journal	May 2016
Synthesis of Bimetallic Uranium and Neptunium Complexes of a Binucleating Macrocycle and Determination of the Solid-State Structure by Magnetic Analysis Arnold, Polly L.; Potter (née Jones), Natalie A.; Magnani, Nicola Inorganic Chemistry, Vol. 49, Issue 12 https://doi.org/10.1021/ic100374j	journal	May 2010
A Metal–Organic Framework Based on a Tetra-Arylextended Calix[4]pyrrole Ligand: Structure Control through the Covalent Connectivity of the Linker Aguilera-Sigalat, Jordi; Sáenz de Pipaón, Cristina; Hernández-Alonso, Daniel Crystal Growth & Design, Vol. 17, Issue 3 https://doi.org/10.1021/acs.cgd.6b01732	journal	January 2017
Ship in a breakable bottle: fluoride-induced release of an organic molecule from a Pr( iii )-linked molecular cage Lee, Juhoon; Waggoner, Nolan W.; Polanco, Luis Chemical Communications, Vol. 52, Issue 55 https://doi.org/10.1039/C6CC03471C	journal	January 2016

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