Controlled distortion of planar porphyrin by intramolecular N-alkylation

The distortion of aromatic macrocycle is of significant interest for understanding of the π-conjugated system. Herein, porphyrin rings with different distortions were synthesized due to intramolecular N-alkylation by introducing a tetraethylene glycol chain. After binding of the cross-linking group...

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Autores principales:	Yoshihiro Ishimaru, Shigeki Sumida, Masahiro Kawabe, Hiroki Ainai, Masahiro Inahara, Takashi Fujihara, Takeaki Iida
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2021
Materias:	N-Alkylation Porphyrin Distortion Aromaticity Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/f0c2988104e44166a0ad44e2310fa9cd
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spelling	oai:doaj.org-article:f0c2988104e44166a0ad44e2310fa9cd2021-11-06T04:27:37ZControlled distortion of planar porphyrin by intramolecular N-alkylation2211-715610.1016/j.rechem.2021.100228https://doaj.org/article/f0c2988104e44166a0ad44e2310fa9cd2021-01-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S2211715621001338https://doaj.org/toc/2211-7156The distortion of aromatic macrocycle is of significant interest for understanding of the π-conjugated system. Herein, porphyrin rings with different distortions were synthesized due to intramolecular N-alkylation by introducing a tetraethylene glycol chain. After binding of the cross-linking group of tetraethylene glycol chain to the porphyrin phenyl group, intramolecular cyclization using silver tetrafluoroborate afforded two types of intramolecularly cross-linked N-substituted porphyrins that were alkylated at the N21, (22) or N23, (24) positions. We found that intramolecularly cross-linked N-substituted porphyrins in which the pyrrole nitrogen was connected by a tetraethylene glycol chain afforded different distortions of the porphyrin ring depending on the N-alkylated substitution position.Yoshihiro IshimaruShigeki SumidaMasahiro KawabeHiroki AinaiMasahiro InaharaTakashi FujiharaTakeaki IidaElsevierarticleN-AlkylationPorphyrinDistortionAromaticityChemistryQD1-999ENResults in Chemistry, Vol 3, Iss , Pp 100228- (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	N-Alkylation Porphyrin Distortion Aromaticity Chemistry QD1-999
spellingShingle	N-Alkylation Porphyrin Distortion Aromaticity Chemistry QD1-999 Yoshihiro Ishimaru Shigeki Sumida Masahiro Kawabe Hiroki Ainai Masahiro Inahara Takashi Fujihara Takeaki Iida Controlled distortion of planar porphyrin by intramolecular N-alkylation
description	The distortion of aromatic macrocycle is of significant interest for understanding of the π-conjugated system. Herein, porphyrin rings with different distortions were synthesized due to intramolecular N-alkylation by introducing a tetraethylene glycol chain. After binding of the cross-linking group of tetraethylene glycol chain to the porphyrin phenyl group, intramolecular cyclization using silver tetrafluoroborate afforded two types of intramolecularly cross-linked N-substituted porphyrins that were alkylated at the N21, (22) or N23, (24) positions. We found that intramolecularly cross-linked N-substituted porphyrins in which the pyrrole nitrogen was connected by a tetraethylene glycol chain afforded different distortions of the porphyrin ring depending on the N-alkylated substitution position.
format	article
author	Yoshihiro Ishimaru Shigeki Sumida Masahiro Kawabe Hiroki Ainai Masahiro Inahara Takashi Fujihara Takeaki Iida
author_facet	Yoshihiro Ishimaru Shigeki Sumida Masahiro Kawabe Hiroki Ainai Masahiro Inahara Takashi Fujihara Takeaki Iida
author_sort	Yoshihiro Ishimaru
title	Controlled distortion of planar porphyrin by intramolecular N-alkylation
title_short	Controlled distortion of planar porphyrin by intramolecular N-alkylation
title_full	Controlled distortion of planar porphyrin by intramolecular N-alkylation
title_fullStr	Controlled distortion of planar porphyrin by intramolecular N-alkylation
title_full_unstemmed	Controlled distortion of planar porphyrin by intramolecular N-alkylation
title_sort	controlled distortion of planar porphyrin by intramolecular n-alkylation
publisher	Elsevier
publishDate	2021
url	https://doaj.org/article/f0c2988104e44166a0ad44e2310fa9cd
work_keys_str_mv	AT yoshihiroishimaru controlleddistortionofplanarporphyrinbyintramolecularnalkylation AT shigekisumida controlleddistortionofplanarporphyrinbyintramolecularnalkylation AT masahirokawabe controlleddistortionofplanarporphyrinbyintramolecularnalkylation AT hirokiainai controlleddistortionofplanarporphyrinbyintramolecularnalkylation AT masahiroinahara controlleddistortionofplanarporphyrinbyintramolecularnalkylation AT takashifujihara controlleddistortionofplanarporphyrinbyintramolecularnalkylation AT takeakiiida controlleddistortionofplanarporphyrinbyintramolecularnalkylation
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Controlled distortion of planar porphyrin by intramolecular N-alkylation

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