A Fully Conjugated Porphyrin-[36]Octaphyrin-Porphyrin Hybrid Tape Exhibiting Möbius Aromaticity.

Möbius aromaticity NIR absorption expanded porphyrin porphyrin tape transannular bond formation

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783

Informations de publication

Date de publication:
06 Apr 2022
Historique:
received: 02 02 2022
pubmed: 27 2 2022
medline: 27 2 2022
entrez: 26 2 2022
Statut: ppublish

Résumé

Directly meso-meso linked porphyrin-tetrabromo[36]octaphyrin-porphyrin hybrid trimer 10 was successfully synthesized via acid-catalyzed condensation reaction and subsequent oxidation. Zn

Identifiants

pubmed: 35218265
doi: 10.1002/chem.202200328
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e202200328

Subventions

Organisme : Japan Society for the Promotion of Science
ID : JP20K05463 and JP21H05480

Informations de copyright

© 2022 Wiley-VCH GmbH.

Références

 
H. L. Anderson, Chem. Commun. 1999, 2323;
M. G. H. Vicente, L. Jaquinod, K. M. Smith, Chem. Commun. 1999, 1771;
J. R. Reimers, N. S. Hush, M. J. Crossley, J. Porphyrins Phthalocyanines 2002, 6, 795;
S. Fox, R. W. Boyle, Tetrahedron 2006, 62, 10039;
N. Aratani, D. Kim, A. Osuka, Chem. Asian J. 2009, 4, 1172;
C. Jiao, J. Wu, Synlett 2012, 23, 171;
J. P. Lewtak, D. T. Gryko, Chem. Commun. 2012, 48, 10069;
A. M. V. M. Pereira, S. Richeter, C. Jeandon, J.-P. Gisselbrecht, J. Wytko, R. Ruppert, J. Porphyrins Phthalocyanines 2012, 16, 464;
H. Mori, T. Tanaka, A. Osuka, J. Mater. Chem. C 2013, 1, 2500;
M. Grzybowski, K. Skonieczny, H. Butenschön, D. T. Gryko, Angew. Chem. Int. Ed. 2013, 52, 9900;
Angew. Chem. 2013, 125, 10084;
T. Tanaka, A. Osuka, Chem. Soc. Rev. 2015, 44, 943;
T. Tanaka, A. Osuka, Chem. Eur. J. 2018, 24, 17188;
A. S. Hazari, S. Chandra, S. Kar, B. Sarkar, Chem. Eur. J. 2022, e202104550.
 
A. Tsuda, H. Furuta, A. Osuka, Angew. Chem. Int. Ed. 2000, 39, 2549;
Angew. Chem. 2000, 112, 2649;
A. Tsuda, A. Osuka, Science 2001, 293, 79;
A. Tsuda, H. Furuta, A. Osuka, J. Am. Chem. Soc. 2001, 123, 10304;
H. S. Cho, D. H. Jeong, S. Cho, D. Kim, Y. Matsuzaki, K. Tanaka, A. Tsuda, A. Osuka, J. Am. Chem. Soc. 2002, 124, 14642.
 
J. L. Sessler, D. Seidel, Angew. Chem. Int. Ed. 2003, 42, 5134;
Angew. Chem. 2003, 115, 5292;
T. K. Chandrashekar, S. Venkatraman, Acc. Chem. Res. 2003, 36, 676;
S. Shimizu, A. Osuka, J. Porphyrins Phthalocyanines 2004, 8, 175;
M. Stępień, N. Sprutta, L. Latos-Grażyński, Angew. Chem. Int. Ed. 2011, 50, 4288;
Angew. Chem. 2011, 123, 4376;
S. Saito, A. Osuka, Angew. Chem. Int. Ed. 2011, 50, 4342;
Angew. Chem. 2011, 123, 4432;
T. Tanaka, A. Osuka, Chem. Rev. 2017, 117, 2584;
B. Szyszko, M. J. Białek, E. Pacholska-Dudziak, L. Latos-Grażyński, Chem. Rev. 2017, 117, 2839.
 
T. Tanaka, N. Aratani, J. M. Lim, K. S. Kim, D. Kim, A. Osuka, Chem. Sci. 2011, 2, 1414;
T. Tanaka, N. Aratani, A. Osuka, Chem. Asian J. 2012, 7, 889;
H. Mori, T. Tanaka, S. Lee, J. M. Lim, D. Kim, A. Osuka J. Am. Chem. Soc. 2015, 137, 2097.
A. Nakai, J. Kim, T. Tanaka, D. Kim, A. Osuka, Angew. Chem. Int. Ed. 2021, 60, 26540;
Angew. Chem. 2021, 133, 26744.
J. M. Lim, J.-Y. Shin, Y. Tanaka, S. Saito, A. Osuka, D. Kim, J. Am. Chem. Soc. 2010, 132, 3105.
 
H. Mori, K. Naoda, A. Osuka, Asian J. Org. Chem. 2013, 2, 600;
K. Ueta, A. Nakai, T. Tanaka, A. Osuka, Chem. Asian J. 2021, 16, 2253.
Usual figure-eight [36]octaphyrins were assigned as nonaromatic compounds; J.-Y. Shin, H. Furuta, K. Yoza, S. Igarashi, A. Osuka, J. Am. Chem. Soc. 2001, 123, 7190.
Deposition Number 2145565 (11) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe http://www.ccdc.cam.ac.uk/structures Access Structures service.
Deposition Number 2145566 (12) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe http://www.ccdc.cam.ac.uk/structures Access Structures service.
Such shifts were also observed for porphyrin-hexaphyrin hybrid trimers and tapes. See Ref. [4].
S.-i. Ishida, J. Kim, D. Shimizu, D. Kim, A. Osuka, Angew. Chem. Int. Ed. 2018, 57, 5876;
Angew. Chem. 2018, 130, 5978.
DFT calculations were performed at the level, B3LYP/6-31G (d) for C, H, N, F, Br and LANL2DZ for Ni, Zn, using the Gaussian 16 program. See the Supporting Information for full citation.
A similar red-shift was observed in the case of porphyrin tapes: T. Ikeue, N. Aratani, A. Osuka, Isr. J. Chem. 2005, 45, 293.

Auteurs

Akito Nakai (A)

Department of Chemistry, Graduate School of Science, Kyoto University Sakyo-ku, Kyoto, 606-8502, Japan.

Takayuki Tanaka (T)

Department of Chemistry, Graduate School of Science, Kyoto University Sakyo-ku, Kyoto, 606-8502, Japan.

Atsuhiro Osuka (A)

Department of Chemistry, Graduate School of Science, Kyoto University Sakyo-ku, Kyoto, 606-8502, Japan.

Classifications MeSH