UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex
Abstract
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+).
- Authors:
-
- Univ. of Texas, Austin, TX (United States)
- Publication Date:
- Research Org.:
- Univ. of Texas, Austin, TX (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); Robert A. Welch Foundation; National Institutes of Health (NIH)
- OSTI Identifier:
- 1598883
- Grant/Contract Number:
- FG02-01ER15186; F-0018; 1-S10-OD021508-01
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Chemical Science
- Additional Journal Information:
- Journal Volume: 10; Journal Issue: 21; Journal ID: ISSN 2041-6520
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Brewster, James T., Root, Harrison D., Mangel, Daniel, Samia, Adam, Zafar, Hadiqa, Sedgwick, Adam C., Lynch, Vincent M., and Sessler, Jonathan L. UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex. United States: N. p., 2019.
Web. doi:10.1039/C9SC01593K.
Brewster, James T., Root, Harrison D., Mangel, Daniel, Samia, Adam, Zafar, Hadiqa, Sedgwick, Adam C., Lynch, Vincent M., & Sessler, Jonathan L. UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex. United States. https://doi.org/10.1039/C9SC01593K
Brewster, James T., Root, Harrison D., Mangel, Daniel, Samia, Adam, Zafar, Hadiqa, Sedgwick, Adam C., Lynch, Vincent M., and Sessler, Jonathan L. Tue .
"UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex". United States. https://doi.org/10.1039/C9SC01593K. https://www.osti.gov/servlets/purl/1598883.
@article{osti_1598883,
title = {UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex},
author = {Brewster, James T. and Root, Harrison D. and Mangel, Daniel and Samia, Adam and Zafar, Hadiqa and Sedgwick, Adam C. and Lynch, Vincent M. and Sessler, Jonathan L.},
abstractNote = {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+).},
doi = {10.1039/C9SC01593K},
journal = {Chemical Science},
number = 21,
volume = 10,
place = {United States},
year = {Tue Apr 30 00:00:00 EDT 2019},
month = {Tue Apr 30 00:00:00 EDT 2019}
}
Web of Science
Works referenced in this record:
Annulated Isomeric, Expanded, and Contracted Porphyrins
journal, November 2016
- Sarma, Tridib; Panda, Pradeepta K.
- Chemical Reviews, Vol. 117, Issue 4
Photoinduced electron transfer in supramolecular systems for artificial photosynthesis
journal, May 1992
- Wasielewski, Michael R.
- Chemical Reviews, Vol. 92, Issue 3, p. 435-461
Heteroatom-Containing Porphyrin Analogues
journal, November 2016
- Chatterjee, Tamal; Shetti, Vijayendra S.; Sharma, Ritambhara
- Chemical Reviews, Vol. 117, Issue 4
Thermal Splitting of Bis-Cu(II) Octaphyrin(1.1.1.1.1.1.1.1) into Two Cu(II) Porphyrins
journal, March 2004
- Tanaka, Yasuo; Hoshino, Wataru; Shimizu, Soji
- Journal of the American Chemical Society, Vol. 126, Issue 10
Uranyl Functionalization Mediated by Redox-Active Ligands: Generation of O–C Bonds via Acylation
journal, December 2018
- Coughlin, Ezra J.; Qiao, Yusen; Lapsheva, Ekaterina
- Journal of the American Chemical Society, Vol. 141, Issue 2
Hexaphyrin(1.0.1.0.0.0): An Expanded Porphyrin Ligand for the Actinide Cations Uranyl (UO22+) and Neptunyl (NpO2+)
journal, January 2001
- Sessler, Jonathan L.; Seidel, Daniel; Vivian, Anne E.
- Angewandte Chemie International Edition, Vol. 40, Issue 3
Redox Behavior of Cyclo[6]pyrrole in the Formation of a Uranyl Complex
journal, June 2007
- Melfi, Patricia J.; Kim, Sung Kuk; Lee, Jeong Tae
- Inorganic Chemistry, Vol. 46, Issue 13
Speciation of uranium: Compilation of a thermodynamic database and its experimental evaluation using different analytical techniques
other, January 2019
- Mühr-Ebert, Elena L.; Wagner, Frank; Walther, Clemens
- London : Elsevier Ltd.
Syntheses of 19-Nor-3-ketosteroids
journal, January 1960
- Hagiwara, Hikoichi; Noguchi, Shunsaku; Nishikawa, Masamoto
- CHEMICAL & PHARMACEUTICAL BULLETIN, Vol. 8, Issue 1
Synthetic Studies on C-19 Oxygenated Pregnanes
journal, May 1963
- Bagli, Jehan F.; Morand, Peter F.; Gaudry, R.
- The Journal of Organic Chemistry, Vol. 28, Issue 5
Lead tetraacetate oxidation of unsaturated alcohols. Oxide formation and fragmentation
journal, January 1964
- Moriarty, Robert M.; Kapadia, Kishori
- Tetrahedron Letters, Vol. 5, Issue 19
19-Hydroxy steroids. III. Reactions with lead tetraacetate
journal, April 1972
- Kaufman, Morris.; Morand, Peter.; Samad, S. A.
- The Journal of Organic Chemistry, Vol. 37, Issue 7
Novel Aspects of Corrole Chemistry
journal, October 2005
- Nardis, Sara; Monti, Donato; Paolesse, Roberto
- Mini-Reviews in Organic Chemistry, Vol. 2, Issue 4
Corrole-Based Applications
journal, August 2007
- Aviv, Iris; Gross, Zeev
- ChemInform, Vol. 38, Issue 35
Fighting Cancer with Corroles
journal, October 2016
- Teo, Ruijie D.; Hwang, Jae Youn; Termini, John
- Chemical Reviews, Vol. 117, Issue 4
meso -Trifluoromethyl-substituted Subporphyrin from Ring-splitting Reaction of meso -Trifluoromethyl-substituted [32]Heptaphyrin(1.1.1.1.1.1.1)
journal, May 2010
- Sakamoto, Ryu; Saito, Shohei; Shimizu, Soji
- Chemistry Letters, Vol. 39, Issue 5
A Hybrid Macrocycle with a Pyridine Subunit Displays Aromatic Character upon Uranyl Cation Complexation
journal, March 2014
- Ho, I-Ting; Zhang, Zhan; Ishida, Masatoshi
- Journal of the American Chemical Society, Vol. 136, Issue 11
The occurrence and roles of porphyrins in the environment: possible implications for bioremediation
journal, August 1993
- Lesage, Suzanne; Xu, Hao; Durham, Louise
- Hydrological Sciences Journal, Vol. 38, Issue 4
Synthesis of Calix[3]dipyrrins by a Modified Lindsey Protocol
journal, March 2007
- Inoue, Mitsunori; Ikeda, Chusaku; Kawata, Yuji
- Angewandte Chemie International Edition, Vol. 46, Issue 13
Isocorroles: Novel Tetrapyrrolic Macrocycles
journal, December 1990
- Will, Stefan; Rahbar, Afssaneh; Schmickler, Hans
- Angewandte Chemie International Edition in English, Vol. 29, Issue 12
Macrocycle Contraction and Expansion of a Dihydrosapphyrin Isomer
journal, December 2013
- Xie, Yongshu; Wei, Pingchun; Li, Xin
- Journal of the American Chemical Society, Vol. 135, Issue 51
Boron(III) Induced Skeletal Rearrangement of Hexaphyrin(1.1.1.1.1.1) to Hexaphyrin(2.1.1.0.1.1)
journal, May 2010
- Moriya, Kohei; Saito, Shohei; Osuka, Atsuhiro
- Angewandte Chemie, Vol. 122, Issue 25
Speciation of uranium: Compilation of a thermodynamic database and its experimental evaluation using different analytical techniques
journal, January 2019
- Mühr-Ebert, Elena L.; Wagner, Frank; Walther, Clemens
- Applied Geochemistry, Vol. 100
Metal coordination induced ring contraction of porphyrin derivatives
journal, January 2018
- Patra, Bratati; Sobottka, Sebastian; Mondal, Sruti
- Chemical Communications, Vol. 54, Issue 71
Comments on Recent Achievements in Biomimetic Organic Synthesis.
journal, March 2004
- de la Torre, Maria C.; Sierra, Miguel A.
- ChemInform, Vol. 35, Issue 13
π-Extended isomeric and expanded porphyrins
journal, January 2013
- Roznyatovskiy, Vladimir V.; Lee, Chang-Hee; Sessler, Jonathan L.
- Chem. Soc. Rev., Vol. 42, Issue 5
Metalloporphyrins – An Update
journal, January 2012
- Schulz, Stephanie; Wong, Ronald J.; Vreman, Hendrik J.
- Frontiers in Pharmacology, Vol. 3
Synthesis and characterization of an amethyrin-uranyl complex displaying aromatic character
text, January 2018
- Brewster, James T.; Aguilar, Apolonio; Anguera, Gonzalo
- Figshare
Strategies for Corrole Functionalization
journal, November 2016
- Barata, Joana F. B.; Neves, M. Graça P. M. S.; Faustino, M. Amparo F.
- Chemical Reviews, Vol. 117, Issue 4
Modified Expanded Corrole-Ferrocene Conjugates: Syntheses, Structure and Properties
journal, September 2005
- Kumar, Rajeev; Misra, Rajneesh; PrabhuRaja, Viswanathan
- Chemistry - A European Journal, Vol. 11, Issue 19
Mechanism of the ring contraction process in vitamin B12 biosynthesis by the anaerobe Propionibacterium shermanii under aerobic conditions: Ring contraction mechanism of vitamin B12
journal, June 2007
- Iida, Katsumi; Ohtaka, Kuniaki; Kajiwara, Masahiro
- FEBS Journal, Vol. 274, Issue 13
An Expanded Porphycene with High NIR Absorptivity That Stabilizes Two Different Kinds of Metal Complexes
journal, January 2018
- Anguera, Gonzalo; Cha, Won-Young; Moore, Matthew D.
- Angewandte Chemie, Vol. 130, Issue 10
Syntheses and Functionalizations of Porphyrin Macrocycles
journal, April 2014
- Vicente, Maria; Smith, Kevin
- Current Organic Synthesis, Vol. 11, Issue 1
Synthesis of Calix[3]dipyrrins by a Modified Lindsey Protocol
journal, March 2007
- Inoue, Mitsunori; Ikeda, Chusaku; Kawata, Yuji
- Angewandte Chemie, Vol. 119, Issue 13
New Transition-State Models and Kinetics of Elimination Reactions of Tertiary Alcohols over Aluminum Oxide
journal, October 1998
- Dabbagh, H. A.; Mohammad Salehi, J.
- The Journal of Organic Chemistry, Vol. 63, Issue 22
Skeletal Rearrangement of Twisted Thia‐Norhexaphyrin: Multiply Annulated Polypyrrolic Aromatic Macrocycles
journal, April 2019
- Li, Qizhao; Ishida, Masatoshi; Kai, Hiroto
- Angewandte Chemie International Edition, Vol. 58, Issue 18
Gold(III) Triggered Transformations of 22-Methyl- m -benziporphyrin Involving an Effective Contraction of Benzene to Cyclopentadiene
journal, December 2016
- Hurej, Karolina; Pawlicki, Miłosz; Latos-Grażyński, Lechosław
- Chemistry - A European Journal, Vol. 23, Issue 9
An Expanded Porphycene with High NIR Absorptivity That Stabilizes Two Different Kinds of Metal Complexes
journal, January 2018
- Anguera, Gonzalo; Cha, Won-Young; Moore, Matthew D.
- Angewandte Chemie International Edition, Vol. 57, Issue 10
The Chemistry of Cyclopropanols
journal, July 2003
- Kulinkovich, Oleg G.
- Chemical Reviews, Vol. 103, Issue 7
Biogenic U(IV) oxidation by dissolved oxygen and nitrate in sediment after prolonged U(VI)/Fe(III)/SO42− reduction
journal, February 2009
- Moon, H. S.; Komlos, J.; Jaffé, P. R.
- Journal of Contaminant Hydrology, Vol. 105, Issue 1-2
Aromaticity switching via azulene transformations in azulene-bridged A,D-dithiahexaphyrin
journal, January 2018
- Białek, Michał J.; Latos-Grażyński, Lechosław
- Chemical Communications, Vol. 54, Issue 15
Porphyrins at interfaces
journal, January 2015
- Auwärter, Willi; Écija, David; Klappenberger, Florian
- Nature Chemistry, Vol. 7, Issue 2
Synthesis and characterization of an amethyrin-uranyl complex displaying aromatic character
journal, April 2018
- Brewster, James T.; Aguilar, Apolonio; Anguera, Gonzalo
- Journal of Coordination Chemistry, Vol. 71, Issue 11-13
A Rhodium-Mediated Contraction of Benzene to Cyclopentadiene: Transformations of Rhodium(III) m -Benziporphyrin
journal, December 2015
- Hurej, Karolina; Pawlicki, Miłosz; Szterenberg, Ludmiła
- Angewandte Chemie International Edition, Vol. 55, Issue 4
Core-Modified Smaragdyrins: First Examples of Stable Meso-Substituted Expanded Corrole
journal, August 1999
- Narayanan, Seenichamy Jeyaprakash; Sridevi, Bashyam; Chandrashekar, Tavarekere K.
- Organic Letters, Vol. 1, Issue 4
Aerobic synthesis of vitamin B12: ring contraction and cobalt chelation
journal, August 2005
- Heldt, D.; Lawrence, A. D.; Lindenmeyer, M.
- Biochemical Society Transactions, Vol. 33, Issue 4
Synthetic Expanded Porphyrin Chemistry
journal, November 2003
- Sessler, Jonathan L.; Seidel, Daniel
- Angewandte Chemie International Edition, Vol. 42, Issue 42
Biosynthesis of cobalamin (vitamin B12)
journal, August 2002
- Scott, A. I.; Roessner, C. A.
- Biochemical Society Transactions, Vol. 30, Issue 4
Nucleophilic attack at the meso position of a uranyl sapphyrin complex
journal, January 1991
- Burrell, Anthony K.; Cyr, Michael J.; Lynch, Vincent
- Journal of the Chemical Society, Chemical Communications, Issue 24
Boron(III) Induced Skeletal Rearrangement of Hexaphyrin(1.1.1.1.1.1) to Hexaphyrin(2.1.1.0.1.1)
journal, May 2010
- Moriya, Kohei; Saito, Shohei; Osuka, Atsuhiro
- Angewandte Chemie International Edition, Vol. 49, Issue 25
Hexaalkyl Terpyrrole: A New Building Block for the Preparation of Expanded Porphyrins
journal, April 1995
- Sessler, Jonathan L.; Weghorn, Steven J.; Hiseada, Yoshio
- Chemistry - A European Journal, Vol. 1, Issue 1
Skeletal Rearrangement of Twisted Thia‐Norhexaphyrin: Multiply Annulated Polypyrrolic Aromatic Macrocycles
journal, April 2019
- Li, Qizhao; Ishida, Masatoshi; Kai, Hiroto
- Angewandte Chemie, Vol. 131, Issue 18
Palladium(II), Ruthenium(II), and Ruthenium(III) Complexes of 23-Thiaazuliporphyrin: The Case of Coordination-Induced Contraction
journal, January 2016
- Białek, Michał J.; Latos-Grażyński, Lechosław
- Inorganic Chemistry, Vol. 55, Issue 4
Biscopper Complexes of meso -Aryl-Substituted Hexaphyrin: Gable Structures and Varying Antiferromagnetic Coupling
journal, October 2004
- Shimizu, Soji; Anand, Venkataramanarao G.; Taniguchi, Ryuichiro
- Journal of the American Chemical Society, Vol. 126, Issue 39
Cryptand-like Porphyrinoid Assembled with Three Dipyrrylpyridine Chains: Synthesis, Structure, and Homotropic Positive Allosteric Binding of Carboxylic Acids
journal, February 2008
- Setsune, Jun-ichiro; Watanabe, Keigo
- Journal of the American Chemical Society, Vol. 130, Issue 8
Anisotropy of the Induced Current Density (ACID), a General Method To Quantify and Visualize Electronic Delocalization
journal, October 2005
- Geuenich, Daniel; Hess, Kirsten; Köhler, Felix
- Chemical Reviews, Vol. 105, Issue 10
Expanded Porphyrins: Intriguing Structures, Electronic Properties, and Reactivities
journal, April 2011
- Saito, Shohei; Osuka, Atsuhiro
- Angewandte Chemie International Edition, Vol. 50, Issue 19
Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO 2 2+ ) Cation
journal, July 2017
- Anguera, Gonzalo; Brewster, James T.; Moore, Matthew D.
- Inorganic Chemistry, Vol. 56, Issue 16
Highly reactive meso-like positions of dipyrihexaphyrin
journal, January 2012
- Setsune, Jun-ichiro; Yamato, Kyohei
- Chemical Communications, Vol. 48, Issue 37
Organic Reactions at Alumina Surfaces
journal, July 1978
- Posner, Gary H.
- Angewandte Chemie International Edition in English, Vol. 17, Issue 7
Preparation of some sulphur-containing polypyrrolic macrocycles. Sulphur extrusion from a meso-thiaphlorin
journal, January 1970
- Broadhurst, M. J.; Grigg, R.; Johnson, A. W.
- Journal of the Chemical Society D: Chemical Communications, Issue 13
Expanded, Contracted, and Isomeric Porphyrins: Theoretical Aspects
journal, November 2016
- Mack, John
- Chemical Reviews, Vol. 117, Issue 4
Synthetic Expanded Porphyrin Chemistry.
journal, February 2004
- Sessler, Jonathan L.; Seidel, Daniel
- ChemInform, Vol. 35, Issue 8
Core chemistry and skeletal rearrangements of porphyrinoids and metalloporphyrinoids
journal, January 2015
- Szyszko, Bartosz; Latos-Grażyński, Lechosław
- Chemical Society Reviews, Vol. 44, Issue 11
Expanding the Porphycene Core: Modification and Metalation
journal, December 2018
- Brewster, James; Anguera, Gonzalo; Sessler, Jonathan
- Synlett, Vol. 30, Issue 07
Bis-vinylogous Corrole: The First Expanded Corrole
journal, September 1999
- Paolesse, Roberto; Khoury, Richard G.; Della Sala, Fabio
- Angewandte Chemie International Edition, Vol. 38, Issue 17
Corrole-based applications
journal, January 2007
- Aviv, Iris; Gross, Zeev
- Chemical Communications, Issue 20
Synthesis and characterization of a dipyriamethyrin–uranyl complex
journal, January 2017
- Brewster, James T.; He, Qing; Anguera, Gonzalo
- Chemical Communications, Vol. 53, Issue 36
Comments on Recent Achievements in Biomimetic Organic Synthesis
journal, January 2004
- de la Torre, María C.; Sierra, Miguel A.
- Angewandte Chemie International Edition, Vol. 43, Issue 2
Synthesis of Corroles and Their Heteroanalogs
journal, November 2016
- Orłowski, Rafał; Gryko, Dorota; Gryko, Daniel T.
- Chemical Reviews, Vol. 117, Issue 4
Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion
journal, September 2005
- Chen, Zhongfang; Wannere, Chaitanya S.; Corminboeuf, Clémence
- Chemical Reviews, Vol. 105, Issue 10
The Chemistry of Cyclopropanols
journal, September 2003
- Kulinkovich, Oleg G.
- ChemInform, Vol. 34, Issue 38
δ-AMINOLEVULINIC ACID, ITS ROLE IN THE BIOSYNTHESIS OF PORPHYRINS AND PURINES 1
journal, October 1953
- Shemin, David; Russell, Charlotte S.
- Journal of the American Chemical Society, Vol. 75, Issue 19
Novel Aspects of Corrole Chemistry
journal, August 2006
- Nardis, Sara; Monti, Donato; Paolesse, Roberto
- ChemInform, Vol. 37, Issue 33
Rhodium-Induced Reversible C−C Bond Cleavage: Transformations of Rhodium(III) 22-Alkyl- m -benziporphyrins
journal, December 2017
- Hurej, Karolina; Pawlicki, Miłosz; Latos-Grażyński, Lechosław
- Chemistry - A European Journal, Vol. 24, Issue 1
1H NMR Spectroscopic Study of Paramagnetic Lanthanide(III) Texaphyrins. Effect of Axial Ligation
journal, March 1995
- Lisowski, Jerzy; Sessler, Jonathan L.; Lynch, Vincent
- Journal of the American Chemical Society, Vol. 117, Issue 8
A Trigonal Bipyramidal Uranyl Amido Complex: Synthesis and Structural Characterization of [Na(THF) 2 ][UO 2 (N(SiMe 3 ) 2 ) 3 ]
journal, November 2000
- Burns, Carol J.; Clark, David L.; Donohoe, Robert J.
- Inorganic Chemistry, Vol. 39, Issue 24
Characterization of the interactions between neptunyl and plutonyl cations and expanded porphyrins
journal, December 2002
- Sessler, Jonathan L.; Gorden, Anne E. V.; Seidel, Daniel
- Inorganica Chimica Acta, Vol. 341
Corroles as anion chemosensors: exploiting their fluorescence behaviour from solution to solid-supported devices
journal, January 2012
- Santos, Carla I. M.; Oliveira, Elisabete; Barata, Joana F. B.
- Journal of Materials Chemistry, Vol. 22, Issue 27
Global versus Local Aromaticity in Porphyrinoid Macrocycles: Experimental and Theoretical Study of “Imidacene”, an Imidazole-Containing Analogue of Porphycene
journal, July 2003
- Sargent, Andrew L.; Hawkins, Ian C.; Allen, William E.
- Chemistry - A European Journal, Vol. 9, Issue 13
Sulphur extrusion reactions applied to the synthesis of corroles and related systems
journal, January 1972
- Broadhurst, M. J.; Grigg, R.; Johnson, A. W.
- Journal of the Chemical Society, Perkin Transactions 1
Dehydration of alcohols over oxide catalysts -eliminations-stereospecificity and selectivity
journal, October 1979
- Siddhan, S.; Narayanan, K.
- Journal of Catalysis, Vol. 59, Issue 3
Dehydration of Alcohols on Aluminum Oxide
journal, October 1968
- Knözinger, H.
- Angewandte Chemie International Edition in English, Vol. 7, Issue 10
Ring expansions and contractions of metalloporphyrins
journal, January 2008
- Callot, Henry J.
- Dalton Transactions, Issue 45
Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion
journal, January 2006
- Chen, Zhongfang; Wannere, Chaitanya S.; Corminboeuf, Clemence
- ChemInform, Vol. 37, Issue 4
Emerging Applications of Porphyrins and Metalloporphyrins in Biomedicine and Diagnostic Magnetic Resonance Imaging
journal, October 2018
- Imran, Muhammad; Ramzan, Muhammad; Qureshi, Ahmad
- Biosensors, Vol. 8, Issue 4
Electrochemistry of Corroles in Nonaqueous Media
journal, November 2016
- Fang, Yuanyuan; Ou, Zhongping; Kadish, Karl M.
- Chemical Reviews, Vol. 117, Issue 4
Stable meso -Aryl β-Alkyl Hybrid Sapphyrin with a Warped π-Conjugation Circuit and Neo-Confused Sapphyrin-Silver(I) Complex
journal, March 2018
- Mori, Daiki; Yoneda, Tomoki; Hoshino, Tyuji
- Chemistry - An Asian Journal, Vol. 13, Issue 8
Why does nature not use the porphyrin ligand in vitamin B12?
journal, February 1987
- Geno, Maureen K.; Halpern, Jack
- Journal of the American Chemical Society, Vol. 109, Issue 4
Blooming of confused porphyrinoids—fusion, expansion, contraction, and more confusion
journal, January 2012
- Toganoh, Motoki; Furuta, Hiroyuki
- Chem. Commun., Vol. 48, Issue 7
Synthesis and Functionalization of Porphyrins through Organometallic Methodologies
journal, October 2016
- Hiroto, Satoru; Miyake, Yoshihiro; Shinokubo, Hiroshi
- Chemical Reviews, Vol. 117, Issue 4
Porphyrin Biosynthesis. 5. Biosynthesis of Protoporphyrin IX in Harderian Glands
journal, October 1968
- Tomio, J. M.; Grinstein, M.
- European Journal of Biochemistry, Vol. 6, Issue 1
Recent advances in biomimetic natural product synthesis
journal, January 2008
- Bulger, Paul G.; Bagal, Sharan K.; Marquez, Rodolfo
- Natural Product Reports, Vol. 25, Issue 2
Tetrapyrroles: the pigments of life
journal, January 2000
- Battersby, Alan R.
- Natural Product Reports, Vol. 17, Issue 6
Anisotropy of the Induced Current Density (ACID), a General Method to Quantify and Visualize Electronic Delocalization
journal, January 2006
- Geuenich, Daniel; Hess, Kirsten; Koehler, Felix
- ChemInform, Vol. 37, Issue 4
Chemical and Electrochemical Dimerization of BODIPY Compounds: Electrogenerated Chemiluminescent Detection of Dimer Formation
journal, December 2011
- Nepomnyashchii, Alexander B.; Bröring, Martin; Ahrens, Johannes
- Journal of the American Chemical Society, Vol. 133, Issue 48
Synthesis and characterization of an amethyrin-uranyl complex displaying aromatic character
text, January 2018
- Brewster, James T.; Aguilar, Apolonio; Anguera, Gonzalo
- Figshare
Works referencing / citing this record:
Expanded Porphyrin Contraction: From [22]Triphyrin(6.6.0) to [22]Triphyrin(6.5.0)
journal, August 2019
- Pacholska‐Dudziak, Ewa; Hojniak‐Thyssen, Sandra; Latos‐Grażyński, Lechosław
- Chemistry – A European Journal, Vol. 25, Issue 51