UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex

Brewster, James T.; Root, Harrison D.; Mangel, Daniel; Samia, Adam; Zafar, Hadiqa; Sedgwick, Adam C.; Lynch, Vincent M.; Sessler, Jonathan L.

doi:10.1039/C9SC01593K

Title: UO₂²⁺-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex

Journal Article · Tue Apr 30 00:00:00 EDT 2019 · Chemical Science

DOI:https://doi.org/10.1039/C9SC01593K· OSTI ID:1598883

^[1];

^[1]; Samia, Adam ^[1];

^[1];

^[1]; Lynch, Vincent M. ^[1];

^[1]

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

A new mixed hexaphyrin, pyrihexaphyrin (0.1.0.0.1.0) (1), was prepared via an acid catalyzed cyclization between 5,5'-(pyridine-2,6-diyl)bis(pyrrole-2-carbaldehyde) (2) and terpyrrole (3). This expanded porphyrin undergoes a ring contraction upon metallation with uranyl silylamide [UO₂[N(SiMe₃)₂]₂] under anaerobic conditions followed by purification over basic aluminum oxide exposed to air. The uranyl-contracted pyrihexaphyrin (0.0.0.0.1.0) complex (4) produced as a result contains a unique structural architecture and possesses a formally 22 π-electron globally aromatic periphery, as inferred from NMR spectroscopy, single crystal X-ray diffraction, and computational analyses. Support for the proposed contraction mechanism came from experimental data and DFT calculations. Proton NMR and mass spectroscopic analysis provided the first insight into expanded porphyrin-mediated activation of the uranyl dication (UO₂²⁺).

View Accepted Manuscript (DOE)

Cite

Export

Save

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

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

Grant/Contract Number:: FG02-01ER15186; F-0018; 1-S10-OD021508-01

OSTI ID:: 1598883

Journal Information:: Chemical Science, Vol. 10, Issue 21; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 16 works

Citation information provided by
Web of Science

References (97)

Annulated Isomeric, Expanded, and Contracted Porphyrins Sarma, Tridib; Panda, Pradeepta K. Chemical Reviews, Vol. 117, Issue 4 https://doi.org/10.1021/acs.chemrev.6b00411	journal	November 2016
Photoinduced electron transfer in supramolecular systems for artificial photosynthesis Wasielewski, Michael R. Chemical Reviews, Vol. 92, Issue 3, p. 435-461 https://doi.org/10.1021/cr00011a005	journal	May 1992
Heteroatom-Containing Porphyrin Analogues Chatterjee, Tamal; Shetti, Vijayendra S.; Sharma, Ritambhara Chemical Reviews, Vol. 117, Issue 4 https://doi.org/10.1021/acs.chemrev.6b00496	journal	November 2016
Thermal Splitting of Bis-Cu(II) Octaphyrin(1.1.1.1.1.1.1.1) into Two Cu(II) Porphyrins Tanaka, Yasuo; Hoshino, Wataru; Shimizu, Soji Journal of the American Chemical Society, Vol. 126, Issue 10 https://doi.org/10.1021/ja031935t	journal	March 2004
Uranyl Functionalization Mediated by Redox-Active Ligands: Generation of O–C Bonds via Acylation Coughlin, Ezra J.; Qiao, Yusen; Lapsheva, Ekaterina Journal of the American Chemical Society, Vol. 141, Issue 2 https://doi.org/10.1021/jacs.8b11302	journal	December 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
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
Speciation of uranium: Compilation of a thermodynamic database and its experimental evaluation using different analytical techniques Mühr-Ebert, Elena L.; Wagner, Frank; Walther, Clemens London : Elsevier Ltd. https://doi.org/10.15488/9762	other	January 2019
Syntheses of 19-Nor-3-ketosteroids Hagiwara, Hikoichi; Noguchi, Shunsaku; Nishikawa, Masamoto CHEMICAL & PHARMACEUTICAL BULLETIN, Vol. 8, Issue 1 https://doi.org/10.1248/cpb.8.84	journal	January 1960
Synthetic Studies on C-19 Oxygenated Pregnanes Bagli, Jehan F.; Morand, Peter F.; Gaudry, R. The Journal of Organic Chemistry, Vol. 28, Issue 5 https://doi.org/10.1021/jo01040a010	journal	May 1963
Lead tetraacetate oxidation of unsaturated alcohols. Oxide formation and fragmentation Moriarty, Robert M.; Kapadia, Kishori Tetrahedron Letters, Vol. 5, Issue 19 https://doi.org/10.1016/S0040-4039(00)90448-9	journal	January 1964
19-Hydroxy steroids. III. Reactions with lead tetraacetate Kaufman, Morris.; Morand, Peter.; Samad, S. A. The Journal of Organic Chemistry, Vol. 37, Issue 7 https://doi.org/10.1021/jo00972a039	journal	April 1972
Novel Aspects of Corrole Chemistry Nardis, Sara; Monti, Donato; Paolesse, Roberto Mini-Reviews in Organic Chemistry, Vol. 2, Issue 4 https://doi.org/10.2174/157019305774322716	journal	October 2005
Corrole-Based Applications Aviv, Iris; Gross, Zeev ChemInform, Vol. 38, Issue 35 https://doi.org/10.1002/chin.200735243	journal	August 2007
Fighting Cancer with Corroles Teo, Ruijie D.; Hwang, Jae Youn; Termini, John Chemical Reviews, Vol. 117, Issue 4 https://doi.org/10.1021/acs.chemrev.6b00400	journal	October 2016
meso -Trifluoromethyl-substituted Subporphyrin from Ring-splitting Reaction of meso -Trifluoromethyl-substituted [32]Heptaphyrin(1.1.1.1.1.1.1) Sakamoto, Ryu; Saito, Shohei; Shimizu, Soji Chemistry Letters, Vol. 39, Issue 5 https://doi.org/10.1246/cl.2010.439	journal	May 2010
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
The occurrence and roles of porphyrins in the environment: possible implications for bioremediation Lesage, Suzanne; Xu, Hao; Durham, Louise Hydrological Sciences Journal, Vol. 38, Issue 4 https://doi.org/10.1080/02626669309492679	journal	August 1993
Synthesis of Calix[3]dipyrrins by a Modified Lindsey Protocol Inoue, Mitsunori; Ikeda, Chusaku; Kawata, Yuji Angewandte Chemie International Edition, Vol. 46, Issue 13 https://doi.org/10.1002/anie.200604882	journal	March 2007
Isocorroles: Novel Tetrapyrrolic Macrocycles Will, Stefan; Rahbar, Afssaneh; Schmickler, Hans Angewandte Chemie International Edition in English, Vol. 29, Issue 12 https://doi.org/10.1002/anie.199013901	journal	December 1990
Macrocycle Contraction and Expansion of a Dihydrosapphyrin Isomer Xie, Yongshu; Wei, Pingchun; Li, Xin Journal of the American Chemical Society, Vol. 135, Issue 51 https://doi.org/10.1021/ja4112644	journal	December 2013
Boron(III) Induced Skeletal Rearrangement of Hexaphyrin(1.1.1.1.1.1) to Hexaphyrin(2.1.1.0.1.1) Moriya, Kohei; Saito, Shohei; Osuka, Atsuhiro Angewandte Chemie, Vol. 122, Issue 25 https://doi.org/10.1002/ange.201001052	journal	May 2010
Speciation of uranium: Compilation of a thermodynamic database and its experimental evaluation using different analytical techniques Mühr-Ebert, Elena L.; Wagner, Frank; Walther, Clemens Applied Geochemistry, Vol. 100 https://doi.org/10.1016/j.apgeochem.2018.10.006	journal	January 2019
Metal coordination induced ring contraction of porphyrin derivatives Patra, Bratati; Sobottka, Sebastian; Mondal, Sruti Chemical Communications, Vol. 54, Issue 71 https://doi.org/10.1039/C8CC04670K	journal	January 2018
Comments on Recent Achievements in Biomimetic Organic Synthesis. de la Torre, Maria C.; Sierra, Miguel A. ChemInform, Vol. 35, Issue 13 https://doi.org/10.1002/chin.200413265	journal	March 2004
π-Extended isomeric and expanded porphyrins Roznyatovskiy, Vladimir V.; Lee, Chang-Hee; Sessler, Jonathan L. Chem. Soc. Rev., Vol. 42, Issue 5 https://doi.org/10.1039/C2CS35418G	journal	January 2013
Metalloporphyrins – An Update Schulz, Stephanie; Wong, Ronald J.; Vreman, Hendrik J. Frontiers in Pharmacology, Vol. 3 https://doi.org/10.3389/fphar.2012.00068	journal	January 2012
Synthesis and characterization of an amethyrin-uranyl complex displaying aromatic character Brewster, James T.; Aguilar, Apolonio; Anguera, Gonzalo Figshare https://doi.org/10.6084/m9.figshare.6078269	text	January 2018
Strategies for Corrole Functionalization Barata, Joana F. B.; Neves, M. Graça P. M. S.; Faustino, M. Amparo F. Chemical Reviews, Vol. 117, Issue 4 https://doi.org/10.1021/acs.chemrev.6b00476	journal	November 2016
Modified Expanded Corrole-Ferrocene Conjugates: Syntheses, Structure and Properties Kumar, Rajeev; Misra, Rajneesh; PrabhuRaja, Viswanathan Chemistry - A European Journal, Vol. 11, Issue 19 https://doi.org/10.1002/chem.200500109	journal	September 2005
Mechanism of the ring contraction process in vitamin B12 biosynthesis by the anaerobe Propionibacterium shermanii under aerobic conditions: Ring contraction mechanism of vitamin B12 Iida, Katsumi; Ohtaka, Kuniaki; Kajiwara, Masahiro FEBS Journal, Vol. 274, Issue 13 https://doi.org/10.1111/j.1742-4658.2007.05880.x	journal	June 2007
An Expanded Porphycene with High NIR Absorptivity That Stabilizes Two Different Kinds of Metal Complexes Anguera, Gonzalo; Cha, Won-Young; Moore, Matthew D. Angewandte Chemie, Vol. 130, Issue 10 https://doi.org/10.1002/ange.201711197	journal	January 2018
Syntheses and Functionalizations of Porphyrin Macrocycles Vicente, Maria; Smith, Kevin Current Organic Synthesis, Vol. 11, Issue 1 https://doi.org/10.2174/15701794113106660083	journal	April 2014
Synthesis of Calix[3]dipyrrins by a Modified Lindsey Protocol Inoue, Mitsunori; Ikeda, Chusaku; Kawata, Yuji Angewandte Chemie, Vol. 119, Issue 13 https://doi.org/10.1002/ange.200604882	journal	March 2007
New Transition-State Models and Kinetics of Elimination Reactions of Tertiary Alcohols over Aluminum Oxide Dabbagh, H. A.; Mohammad Salehi, J. The Journal of Organic Chemistry, Vol. 63, Issue 22 https://doi.org/10.1021/jo971609u	journal	October 1998
Skeletal Rearrangement of Twisted Thia‐Norhexaphyrin: Multiply Annulated Polypyrrolic Aromatic Macrocycles Li, Qizhao; Ishida, Masatoshi; Kai, Hiroto Angewandte Chemie International Edition, Vol. 58, Issue 18 https://doi.org/10.1002/anie.201900010	journal	April 2019
Gold(III) Triggered Transformations of 22-Methyl- m -benziporphyrin Involving an Effective Contraction of Benzene to Cyclopentadiene Hurej, Karolina; Pawlicki, Miłosz; Latos-Grażyński, Lechosław Chemistry - A European Journal, Vol. 23, Issue 9 https://doi.org/10.1002/chem.201604458	journal	December 2016
An Expanded Porphycene with High NIR Absorptivity That Stabilizes Two Different Kinds of Metal Complexes Anguera, Gonzalo; Cha, Won-Young; Moore, Matthew D. Angewandte Chemie International Edition, Vol. 57, Issue 10 https://doi.org/10.1002/anie.201711197	journal	January 2018
The Chemistry of Cyclopropanols Kulinkovich, Oleg G. Chemical Reviews, Vol. 103, Issue 7 https://doi.org/10.1021/cr010012i	journal	July 2003
Biogenic U(IV) oxidation by dissolved oxygen and nitrate in sediment after prolonged U(VI)/Fe(III)/SO42− reduction Moon, H. S.; Komlos, J.; Jaffé, P. R. Journal of Contaminant Hydrology, Vol. 105, Issue 1-2 https://doi.org/10.1016/j.jconhyd.2008.10.014	journal	February 2009
Aromaticity switching via azulene transformations in azulene-bridged A,D-dithiahexaphyrin Białek, Michał J.; Latos-Grażyński, Lechosław Chemical Communications, Vol. 54, Issue 15 https://doi.org/10.1039/C7CC08754C	journal	January 2018
Porphyrins at interfaces Auwärter, Willi; Écija, David; Klappenberger, Florian Nature Chemistry, Vol. 7, Issue 2 https://doi.org/10.1038/nchem.2159	journal	January 2015
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
A Rhodium-Mediated Contraction of Benzene to Cyclopentadiene: Transformations of Rhodium(III) m -Benziporphyrin Hurej, Karolina; Pawlicki, Miłosz; Szterenberg, Ludmiła Angewandte Chemie International Edition, Vol. 55, Issue 4 https://doi.org/10.1002/anie.201508033	journal	December 2015
Core-Modified Smaragdyrins: First Examples of Stable Meso-Substituted Expanded Corrole Narayanan, Seenichamy Jeyaprakash; Sridevi, Bashyam; Chandrashekar, Tavarekere K. Organic Letters, Vol. 1, Issue 4 https://doi.org/10.1021/ol990108n	journal	August 1999
Aerobic synthesis of vitamin B12: ring contraction and cobalt chelation Heldt, D.; Lawrence, A. D.; Lindenmeyer, M. Biochemical Society Transactions, Vol. 33, Issue 4 https://doi.org/10.1042/BST0330815	journal	August 2005
Synthetic Expanded Porphyrin Chemistry Sessler, Jonathan L.; Seidel, Daniel Angewandte Chemie International Edition, Vol. 42, Issue 42 https://doi.org/10.1002/anie.200200561	journal	November 2003
Biosynthesis of cobalamin (vitamin B12) Scott, A. I.; Roessner, C. A. Biochemical Society Transactions, Vol. 30, Issue 4 https://doi.org/10.1042/bst0300613	journal	August 2002
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
Boron(III) Induced Skeletal Rearrangement of Hexaphyrin(1.1.1.1.1.1) to Hexaphyrin(2.1.1.0.1.1) Moriya, Kohei; Saito, Shohei; Osuka, Atsuhiro Angewandte Chemie International Edition, Vol. 49, Issue 25 https://doi.org/10.1002/anie.201001052	journal	May 2010
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
Skeletal Rearrangement of Twisted Thia‐Norhexaphyrin: Multiply Annulated Polypyrrolic Aromatic Macrocycles Li, Qizhao; Ishida, Masatoshi; Kai, Hiroto Angewandte Chemie, Vol. 131, Issue 18 https://doi.org/10.1002/ange.201900010	journal	April 2019
Palladium(II), Ruthenium(II), and Ruthenium(III) Complexes of 23-Thiaazuliporphyrin: The Case of Coordination-Induced Contraction Białek, Michał J.; Latos-Grażyński, Lechosław Inorganic Chemistry, Vol. 55, Issue 4 https://doi.org/10.1021/acs.inorgchem.5b02684	journal	January 2016
Biscopper Complexes of meso -Aryl-Substituted Hexaphyrin: Gable Structures and Varying Antiferromagnetic Coupling Shimizu, Soji; Anand, Venkataramanarao G.; Taniguchi, Ryuichiro Journal of the American Chemical Society, Vol. 126, Issue 39 https://doi.org/10.1021/ja046102x	journal	October 2004
Cryptand-like Porphyrinoid Assembled with Three Dipyrrylpyridine Chains: Synthesis, Structure, and Homotropic Positive Allosteric Binding of Carboxylic Acids Setsune, Jun-ichiro; Watanabe, Keigo Journal of the American Chemical Society, Vol. 130, Issue 8 https://doi.org/10.1021/ja710424n	journal	February 2008
Anisotropy of the Induced Current Density (ACID), a General Method To Quantify and Visualize Electronic Delocalization Geuenich, Daniel; Hess, Kirsten; Köhler, Felix Chemical Reviews, Vol. 105, Issue 10 https://doi.org/10.1021/cr0300901	journal	October 2005
Expanded Porphyrins: Intriguing Structures, Electronic Properties, and Reactivities Saito, Shohei; Osuka, Atsuhiro Angewandte Chemie International Edition, Vol. 50, Issue 19 https://doi.org/10.1002/anie.201003909	journal	April 2011
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
Highly reactive meso-like positions of dipyrihexaphyrin Setsune, Jun-ichiro; Yamato, Kyohei Chemical Communications, Vol. 48, Issue 37 https://doi.org/10.1039/c2cc30981e	journal	January 2012
Organic Reactions at Alumina Surfaces Posner, Gary H. Angewandte Chemie International Edition in English, Vol. 17, Issue 7 https://doi.org/10.1002/anie.197804871	journal	July 1978
Preparation of some sulphur-containing polypyrrolic macrocycles. Sulphur extrusion from a meso-thiaphlorin Broadhurst, M. J.; Grigg, R.; Johnson, A. W. Journal of the Chemical Society D: Chemical Communications, Issue 13 https://doi.org/10.1039/c29700000807	journal	January 1970
Expanded, Contracted, and Isomeric Porphyrins: Theoretical Aspects Mack, John Chemical Reviews, Vol. 117, Issue 4 https://doi.org/10.1021/acs.chemrev.6b00568	journal	November 2016
Synthetic Expanded Porphyrin Chemistry. Sessler, Jonathan L.; Seidel, Daniel ChemInform, Vol. 35, Issue 8 https://doi.org/10.1002/chin.200408288	journal	February 2004
Core chemistry and skeletal rearrangements of porphyrinoids and metalloporphyrinoids Szyszko, Bartosz; Latos-Grażyński, Lechosław Chemical Society Reviews, Vol. 44, Issue 11 https://doi.org/10.1039/C4CS00398E	journal	January 2015
Expanding the Porphycene Core: Modification and Metalation Brewster, James; Anguera, Gonzalo; Sessler, Jonathan Synlett, Vol. 30, Issue 07 https://doi.org/10.1055/s-0037-1610345	journal	December 2018
Bis-vinylogous Corrole: The First Expanded Corrole Paolesse, Roberto; Khoury, Richard G.; Della Sala, Fabio Angewandte Chemie International Edition, Vol. 38, Issue 17 https://doi.org/10.1002/(SICI)1521-3773(19990903)38:17<2577::AID-ANIE2577>3.0.CO;2-G	journal	September 1999
Corrole-based applications Aviv, Iris; Gross, Zeev Chemical Communications, Issue 20 https://doi.org/10.1039/b618482k	journal	January 2007
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
Comments on Recent Achievements in Biomimetic Organic Synthesis de la Torre, María C.; Sierra, Miguel A. Angewandte Chemie International Edition, Vol. 43, Issue 2 https://doi.org/10.1002/anie.200200545	journal	January 2004
Synthesis of Corroles and Their Heteroanalogs Orłowski, Rafał; Gryko, Dorota; Gryko, Daniel T. Chemical Reviews, Vol. 117, Issue 4 https://doi.org/10.1021/acs.chemrev.6b00434	journal	November 2016
Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion Chen, Zhongfang; Wannere, Chaitanya S.; Corminboeuf, Clémence Chemical Reviews, Vol. 105, Issue 10 https://doi.org/10.1021/cr030088+	journal	September 2005
The Chemistry of Cyclopropanols Kulinkovich, Oleg G. ChemInform, Vol. 34, Issue 38 https://doi.org/10.1002/chin.200338261	journal	September 2003
δ-AMINOLEVULINIC ACID, ITS ROLE IN THE BIOSYNTHESIS OF PORPHYRINS AND PURINES ¹ Shemin, David; Russell, Charlotte S. Journal of the American Chemical Society, Vol. 75, Issue 19 https://doi.org/10.1021/ja01115a546	journal	October 1953
Novel Aspects of Corrole Chemistry Nardis, Sara; Monti, Donato; Paolesse, Roberto ChemInform, Vol. 37, Issue 33 https://doi.org/10.1002/chin.200633275	journal	August 2006
Rhodium-Induced Reversible C−C Bond Cleavage: Transformations of Rhodium(III) 22-Alkyl- m -benziporphyrins Hurej, Karolina; Pawlicki, Miłosz; Latos-Grażyński, Lechosław Chemistry - A European Journal, Vol. 24, Issue 1 https://doi.org/10.1002/chem.201704411	journal	December 2017
1H NMR Spectroscopic Study of Paramagnetic Lanthanide(III) Texaphyrins. Effect of Axial Ligation Lisowski, Jerzy; Sessler, Jonathan L.; Lynch, Vincent Journal of the American Chemical Society, Vol. 117, Issue 8 https://doi.org/10.1021/ja00113a016	journal	March 1995
A Trigonal Bipyramidal Uranyl Amido Complex: Synthesis and Structural Characterization of [Na(THF) ₂ ][UO ₂ (N(SiMe ₃ ) ₂ ) ₃ ] Burns, Carol J.; Clark, David L.; Donohoe, Robert J. Inorganic Chemistry, Vol. 39, Issue 24 https://doi.org/10.1021/ic0003168	journal	November 2000
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
Corroles as anion chemosensors: exploiting their fluorescence behaviour from solution to solid-supported devices Santos, Carla I. M.; Oliveira, Elisabete; Barata, Joana F. B. Journal of Materials Chemistry, Vol. 22, Issue 27 https://doi.org/10.1039/c2jm31281f	journal	January 2012
Global versus Local Aromaticity in Porphyrinoid Macrocycles: Experimental and Theoretical Study of “Imidacene”, an Imidazole-Containing Analogue of Porphycene Sargent, Andrew L.; Hawkins, Ian C.; Allen, William E. Chemistry - A European Journal, Vol. 9, Issue 13 https://doi.org/10.1002/chem.200204694	journal	July 2003
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
Dehydration of alcohols over oxide catalysts -eliminations-stereospecificity and selectivity Siddhan, S.; Narayanan, K. Journal of Catalysis, Vol. 59, Issue 3 https://doi.org/10.1016/S0021-9517(79)80009-3	journal	October 1979
Dehydration of Alcohols on Aluminum Oxide Knözinger, H. Angewandte Chemie International Edition in English, Vol. 7, Issue 10 https://doi.org/10.1002/anie.196807911	journal	October 1968
Ring expansions and contractions of metalloporphyrins Callot, Henry J. Dalton Transactions, Issue 45 https://doi.org/10.1039/b807066k	journal	January 2008
Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion Chen, Zhongfang; Wannere, Chaitanya S.; Corminboeuf, Clemence ChemInform, Vol. 37, Issue 4 https://doi.org/10.1002/chin.200604277	journal	January 2006
Emerging Applications of Porphyrins and Metalloporphyrins in Biomedicine and Diagnostic Magnetic Resonance Imaging Imran, Muhammad; Ramzan, Muhammad; Qureshi, Ahmad Biosensors, Vol. 8, Issue 4 https://doi.org/10.3390/bios8040095	journal	October 2018
Electrochemistry of Corroles in Nonaqueous Media Fang, Yuanyuan; Ou, Zhongping; Kadish, Karl M. Chemical Reviews, Vol. 117, Issue 4 https://doi.org/10.1021/acs.chemrev.6b00546	journal	November 2016
Stable meso -Aryl β-Alkyl Hybrid Sapphyrin with a Warped π-Conjugation Circuit and Neo-Confused Sapphyrin-Silver(I) Complex Mori, Daiki; Yoneda, Tomoki; Hoshino, Tyuji Chemistry - An Asian Journal, Vol. 13, Issue 8 https://doi.org/10.1002/asia.201800286	journal	March 2018
Why does nature not use the porphyrin ligand in vitamin B12? Geno, Maureen K.; Halpern, Jack Journal of the American Chemical Society, Vol. 109, Issue 4 https://doi.org/10.1021/ja00238a039	journal	February 1987
Blooming of confused porphyrinoids—fusion, expansion, contraction, and more confusion Toganoh, Motoki; Furuta, Hiroyuki Chem. Commun., Vol. 48, Issue 7 https://doi.org/10.1039/C1CC14633E	journal	January 2012
Synthesis and Functionalization of Porphyrins through Organometallic Methodologies Hiroto, Satoru; Miyake, Yoshihiro; Shinokubo, Hiroshi Chemical Reviews, Vol. 117, Issue 4 https://doi.org/10.1021/acs.chemrev.6b00427	journal	October 2016
Porphyrin Biosynthesis. 5. Biosynthesis of Protoporphyrin IX in Harderian Glands Tomio, J. M.; Grinstein, M. European Journal of Biochemistry, Vol. 6, Issue 1 https://doi.org/10.1111/j.1432-1033.1968.tb00421.x	journal	October 1968
Recent advances in biomimetic natural product synthesis Bulger, Paul G.; Bagal, Sharan K.; Marquez, Rodolfo Natural Product Reports, Vol. 25, Issue 2 https://doi.org/10.1039/b705909b	journal	January 2008
Tetrapyrroles: the pigments of life Battersby, Alan R. Natural Product Reports, Vol. 17, Issue 6 https://doi.org/10.1039/b002635m	journal	January 2000
Anisotropy of the Induced Current Density (ACID), a General Method to Quantify and Visualize Electronic Delocalization Geuenich, Daniel; Hess, Kirsten; Koehler, Felix ChemInform, Vol. 37, Issue 4 https://doi.org/10.1002/chin.200604280	journal	January 2006
Chemical and Electrochemical Dimerization of BODIPY Compounds: Electrogenerated Chemiluminescent Detection of Dimer Formation Nepomnyashchii, Alexander B.; Bröring, Martin; Ahrens, Johannes Journal of the American Chemical Society, Vol. 133, Issue 48 https://doi.org/10.1021/ja207545t	journal	December 2011
Synthesis and characterization of an amethyrin-uranyl complex displaying aromatic character Brewster, James T.; Aguilar, Apolonio; Anguera, Gonzalo Figshare https://doi.org/10.6084/m9.figshare.6078269.v1	text	January 2018

Cited By (1)

Expanded Porphyrin Contraction: From [22]Triphyrin(6.6.0) to [22]Triphyrin(6.5.0) Pacholska‐Dudziak, Ewa; Hojniak‐Thyssen, Sandra; Latos‐Grażyński, Lechosław Chemistry – A European Journal, Vol. 25, Issue 51 https://doi.org/10.1002/chem.201903181	journal	August 2019

Linked Research (3)

Similar Records

Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO₂²⁺) Cation

Journal Article · Mon Aug 07 00:00:00 EDT 2017 · Inorganic Chemistry · OSTI ID:1598883

Anguera, Gonzalo; Brewster, II, James T.; Moore, Matthew D.; +5 more

Synthesis and characterization of an amethyrin-uranyl complex displaying aromatic character

Journal Article · Fri Apr 20 00:00:00 EDT 2018 · Journal of Coordination Chemistry · OSTI ID:1598883

Brewster, James T.; Aguilar, Apolonio; Anguera, Gonzalo; +3 more

In-Plane Thorium(IV), Uranium(IV), and Neptunium(IV) Expanded Porphyrin Complexes

Journal Article · Mon Oct 14 00:00:00 EDT 2019 · Journal of the American Chemical Society · OSTI ID:1598883

Brewster, James T.; Mangel, Daniel N.; Gaunt, Andrew J.; +9 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

CCDC 1893882: Experimental Crystal Structure Determination T., Brewster, James; D., Root, Harrison; Daniel, Mangel, https://doi.org/10.5517/ccdc.csd.cc21kqzb The current record is supplemented by this dataset	dataset	January 2019
CCDC 1893883: Experimental Crystal Structure Determination T., Brewster, James; D., Root, Harrison; Daniel, Mangel, https://doi.org/10.5517/ccdc.csd.cc21kr0d The current record is supplemented by this dataset	dataset	January 2019
CCDC 1893382: Experimental Crystal Structure Determination Shu-Li, Qian,; Meng-Lei, Le,; Xiao-Hui, Wu, https://doi.org/10.5517/ccdc.csd.cc21k6vp The current record is supplemented by this dataset	dataset	January 2019

Title: UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex

Citation Formats