Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/an-overall-comprehension-of-anti-aromatic-porphyrinoids-using-3d-C5MJ9LkiIV
References (46)
-
Gang Sun, Xi-Xin Duan, Chun-Hui Yu, Chun-Guan Liu (2015)
Theoretical investigation of the aromaticity and electronic properties of protonated and unprotonated molecules in the series hexaphyrin(1.0.0.1.0.0) to hexaphyrin(1.1.1.1.1.1)Journal of Molecular Modeling, 21
-
Martin Johnson, C. Slebodnick, J. Ibers (1997)
Synthesis and characterization of a new [4.0.4.0] porphyrin‐like antiaromatic macrocycleJournal of Porphyrins and Phthalocyanines, 1
-
The IDRs of Ref-1 and Ref-2 are also calculated at the level of M06-2X/6-311+G(2d,p) -
J. Reddy, V. Anand (2008)
Planar meso pentafluorophenyl core modified isophlorins.Journal of the American Chemical Society, 130 12
-
T. Lu, Feiwu Chen (2012)
Multiwfn: A multifunctional wavefunction analyzerJournal of Computational Chemistry, 33
-
Y. Sung, Juwon Oh, Won‐Young Cha, Woojae Kim, Jong Lim, Min-Chul Yoon, Dongho Kim (2017)
Control and Switching of Aromaticity in Various All-Aza-Expanded Porphyrins: Spectroscopic and Theoretical Analyses.Chemical reviews, 117 4
-
Masatoshi Ishida, S. Kim, Christian Preihs, K. Ohkubo, Jong Lim, Byung Lee, J. Park, V. Lynch, Vladimir Roznyatovskiy, T. Sarma, P. Panda, Chang-Hee Lee, S. Fukuzumi, Dongho Kim, J. Sessler (2013)
Protonation-coupled redox reactions in planar antiaromatic meso-pentafluorophenyl-substituted o-phenylene-bridged annulated rosarins.Nature chemistry, 5 1
-
Ryouichi Nozawa, Hiroko Tanaka, Won‐Young Cha, Yongseok Hong, Ichiro Hisaki, Soji Shimizu, Ji-Young Shin, T. Kowalczyk, S. Irle, Dongho Kim, H. Shinokubo (2016)
Stacked antiaromatic porphyrinsNature Communications, 7
-
Satoru Hiroto, H. Shinokubo (2016)
Syntheses and Properties of Antiaromatic Porphyrinoids -
Daiki Kuzuhara, H. Yamada, K. Yano, T. Okujima, Shigeki Mori, H. Uno (2011)
First synthesis of dodecasubstituted porphycenes.Chemistry, 17 12
-
J. Aihara (2008)
Macrocyclic conjugation pathways in porphyrins.The journal of physical chemistry. A, 112 23
-
E. Hückel (1932)
Quantentheoretische Beiträge zum Problem der aromatischen und ungesättigten Verbindungen. IIIZeitschrift für Physik, 76
-
M. Takase, V. Enkelmann, D. Sebastiani, M. Baumgarten, K. Müllen (2007)
Annularly fused hexapyrrolohexaazacoronenes: an extended pi system with multiple interior nitrogen atoms displays stable oxidation states.Angewandte Chemie, 46 29
-
K. Kadish, Kevin Smith, R. Guilard (2019)
Handbook of Porphyrin ScienceHandbook of Porphyrin Science
-
B. Reddy, A. Basavarajappa, Madan Ambhore, V. Anand (2017)
Isophlorinoids: The Antiaromatic Congeners of Porphyrinoids.Chemical reviews, 117 4
-
Théo Gonçalves, Kuo‐Wei Huang (2017)
Metal-Ligand Cooperative Reactivity in the (Pseudo)-Dearomatized PNx(P) Systems: The Influence of the Zwitterionic Form in Dearomatized Pincer Complexes.Journal of the American Chemical Society, 139 38
-
Florence Szydlo, B. Andrioletti, E. Rose (2006)
Facile preparation of doubly dipyrrolylquinoxaline-bridged expanded porphyrins. Synthesis and structural characterization of an unprecedented [20]tetraphyrin-(2.1.2.1).Organic letters, 8 11
-
S. Klod, E. Kleinpeter, T. Lu (2001)
Multiwfn Manual (Version 3.6) -
Kamil Kupietz, Michał Białek, A. Białońska, B. Szyszko, L. Latos‐Grażyński (2018)
Aromaticity control via modifications of a macrocyclic frame: 5,6-dimethoxyphenanthriporphyrin and 5,6-dioxophenanthriporphyrinOrganic chemistry frontiers, 5
-
Akihide Nishiyama, Masaya Fukuda, Shigeki Mori, K. Furukawa, Heike Fliegl, H. Furuta, Soji Shimizu (2018)
Rational Synthesis of Antiaromatic 5,15-Dioxaporphyrin and Oxidation into β,β-Linked Dimers.Angewandte Chemie, 57 31
-
Wenbo Liu, H. Pan, Ziqian Wang, Kang Wang, Dongdong Qi, Jianzhuang Jiang (2017)
Sandwich rare earth complexes simultaneously involving aromatic phthalocyanine and antiaromatic hemiporphyrazine ligands showing a predominantly aromatic nature.Chemical communications, 53 26
-
E. Vogel, Ilona Grigat, Matthias Köcher, J. Lex (1989)
A Pyrrolophanediene-Porphycene Redox SystemAngewandte Chemie, 28
-
I. Rabi, J. Zacharias, S. Millman, P. Kusch (1938)
A New Method of Measuring Nuclear Magnetic MomentPhysical Review, 53
-
T. Lu, T. Lu, F. Chen (2016)
Multiwfn Software Manual (Vesrion 3.3.9), 33
-
E. Hückel (1937)
Grundzüge der Theorie ungesättigter und aromatischer VerbindungenZeitschrift für Elektrochemie und angewandte physikalische Chemie
-
P. Karadakov, Kate Horner (2016)
Exploring Chemical Bonds through Variations in Magnetic Shielding.Journal of chemical theory and computation, 12 2
-
Yan Zhao, D. Truhlar (2006)
A new local density functional for main-group thermochemistry, transition metal bonding, thermochemical kinetics, and noncovalent interactions.The Journal of chemical physics, 125 19
-
P. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. Hommes (1996)
Nucleus-Independent Chemical Shifts: A Simple and Efficient Aromaticity Probe.Journal of the American Chemical Society, 118 26
-
(1937)
Phys. 1931, 70, 204; b) E. Hückel, Z. Phys. 1932, 76, 628; c) E. Hückel -
R. Krishnan, J. Binkley, R. Seeger, J. Pople (1980)
Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functionsJournal of Chemical Physics, 72
-
(2016)
For example : a ) P . B . Karadakov , K . E . Horner -
T. Krygowski, B. Stępień (2005)
Sigma- and pi-electron delocalization: focus on substituent effects.Chemical reviews, 105 10
-
Takafumi Sakida, S. Yamaguchi, H. Shinokubo (2011)
Metal-mediated synthesis of antiaromatic porphyrinoids from a BODIPY precursor.Angewandte Chemie, 50 10
-
Simil Thomas, Y. Pati, S. Ramasesha (2013)
Linear and nonlinear optical properties of expanded porphyrins: a DMRG study.The journal of physical chemistry. A, 117 33
-
A. Osuka, Shohei Saito (2011)
Expanded porphyrins and aromaticity.Chemical communications, 47 15
-
Takayuki Tanaka, A. Osuka (2017)
Chemistry of meso-Aryl-Substituted Expanded Porphyrins: Aromaticity and Molecular Twist.Chemical reviews, 117 4
-
T. Matsuo, Kazuyuki Ito, N. Kanehisa, Takashi Hayashi (2007)
A structural isomer of nonaromatic porphyrin: preparation of 20pi-conjugated porphycene based on electronic perturbation.Organic letters, 9 25
-
E. Hückel (1931)
Quanstentheoretische Beiträge zum BenzolproblemZeitschrift für Physik, 72
-
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery (2009)
Gaussian 09 -
Renana Gershoni‐Poranne, A. Stanger (2015)
Magnetic criteria of aromaticity.Chemical Society reviews, 44 18
-
(2012)
Multiwfn Software Manual (Vesrion 3.3.9), Beijing Kein Research Center for Natural Sciences, Beijing, China 2016 -
A. Muranaka, Shino Ohira, N. Toriumi, M. Hirayama, Fumiko Kyotani, Y. Mori, D. Hashizume, M. Uchiyama (2014)
Unraveling the electronic structure of azolehemiporphyrazines: direct spectroscopic observation of magnetic dipole allowed nature of the lowest π-π* transition of 20π-electron porphyrinoids.The journal of physical chemistry. A, 118 25
-
E. Vogel, J. Dörr, A. Herrmann, J. Lex, H. Schmickler, P. Walgenbach, J. Gisselbrecht, M. Gross (1993)
Octaethyltetraoxaporphyrin Dication—Counterpart of Octaethylporphyrin in the Tetraoxaporphyrin SeriesAngewandte Chemie, 32
-
(2012)
Beijing Kein Research Center for Natural Sciences -
Zhongfang Chen, R. King (2005)
Spherical aromaticity: recent work on fullerenes, polyhedral boranes, and related structures.Chemical reviews, 105 10
-
(2003)
The Porphyrin Handbook, 1–20
- Publisher
- Wiley
- Copyright
- © 2020 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
- eISSN
- 2513-0390
- DOI
- 10.1002/adts.202000007
- Publisher site
- See Article on Publisher Site
Abstract
A systematic investigation to rank the anti‐aromatic porphyrinoids is performed. Based on density functional theory calculations, four rules are summarized to obtain the highest anti‐aromatic porphyrinoids: 1) the replacement from meso‐C to meso‐(─C≡C─), 2) the replacement from pyrrole unit to inner‐N to inner‐O, 3) the replacement from two opposite meso‐C/N atoms to two pyrrole units, and 4) the replacement from one pyrrole ring to a carbonyl benzene ring. It is worth noting that the long chain with alternating single/double bonds is not beneficial or harmful to the anti‐aromaticity.
Journal
Advanced Theory and Simulations – Wiley
Published: May 1, 2020
Keywords: ; ;