Carbaporphyrin Dimers That Bear a Rigid Naphthalene Motif as an Internal Strap

Jung Ho Hong; Adil S. Aslam; Beomhee Cho; Min Sung Ko; Younghoon Kim; Jungseok Heo; Dong Gyu Cho

doi:10.1021/acs.orglett.1c00252

Carbaporphyrin Dimers That Bear a Rigid Naphthalene Motif as an Internal Strap

Jung Ho Hong, Adil S. Aslam, Beomhee Cho, Min Sung Ko, Younghoon Kim, Jungseok Heo, Dong Gyu Cho

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

The first fully connected aromatic carbaporphyrin dimer (6) and its bis-Pd complex (6-Pd2) that bear a rigid naphthalene motif as an internal strap were synthesized. These dimers consisted of two aromatic carbaporphyrins that shared a naphthalene motif. The Ï-electron conjugation of the obtained macrocycles was proposed to have two separated local 22 Ï-electron pathways and a 34 Ï-electron pathway. Their weak aromaticity was fully supported by 1H NMR spectroscopy, NICS values, ACID calculations, and ICSS plots.

Original language	English
Pages (from-to)	1846-1850
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.1c00252
State	Published - Mar 5 2021
Externally published	Yes

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title = "Carbaporphyrin Dimers That Bear a Rigid Naphthalene Motif as an Internal Strap",

abstract = "The first fully connected aromatic carbaporphyrin dimer (6) and its bis-Pd complex (6-Pd2) that bear a rigid naphthalene motif as an internal strap were synthesized. These dimers consisted of two aromatic carbaporphyrins that shared a naphthalene motif. The {\"I}-electron conjugation of the obtained macrocycles was proposed to have two separated local 22 {\"I}-electron pathways and a 34 {\"I}-electron pathway. Their weak aromaticity was fully supported by 1H NMR spectroscopy, NICS values, ACID calculations, and ICSS plots.",

author = "Hong, {Jung Ho} and Aslam, {Adil S.} and Beomhee Cho and Ko, {Min Sung} and Younghoon Kim and Jungseok Heo and Cho, {Dong Gyu}",

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T1 - Carbaporphyrin Dimers That Bear a Rigid Naphthalene Motif as an Internal Strap

AU - Hong, Jung Ho

AU - Aslam, Adil S.

AU - Cho, Beomhee

AU - Ko, Min Sung

AU - Kim, Younghoon

AU - Heo, Jungseok

AU - Cho, Dong Gyu

N1 - Publisher Copyright: ©

PY - 2021/3/5

Y1 - 2021/3/5

N2 - The first fully connected aromatic carbaporphyrin dimer (6) and its bis-Pd complex (6-Pd2) that bear a rigid naphthalene motif as an internal strap were synthesized. These dimers consisted of two aromatic carbaporphyrins that shared a naphthalene motif. The Ï-electron conjugation of the obtained macrocycles was proposed to have two separated local 22 Ï-electron pathways and a 34 Ï-electron pathway. Their weak aromaticity was fully supported by 1H NMR spectroscopy, NICS values, ACID calculations, and ICSS plots.

AB - The first fully connected aromatic carbaporphyrin dimer (6) and its bis-Pd complex (6-Pd2) that bear a rigid naphthalene motif as an internal strap were synthesized. These dimers consisted of two aromatic carbaporphyrins that shared a naphthalene motif. The Ï-electron conjugation of the obtained macrocycles was proposed to have two separated local 22 Ï-electron pathways and a 34 Ï-electron pathway. Their weak aromaticity was fully supported by 1H NMR spectroscopy, NICS values, ACID calculations, and ICSS plots.

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SN - 1523-7060

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SP - 1846

EP - 1850

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Carbaporphyrin Dimers That Bear a Rigid Naphthalene Motif as an Internal Strap

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