Cyclic 2,12-porphyrinylene nanorings as a porphyrin analogue of cycloparaphenylenes

Hua Wei Jiang; Takayuki Tanaka; Hirotaka Mori; Kyu Hyung Park; Dongho Kim; Atsuhiro Osuka

doi:10.1021/ja513102m

Cyclic 2,12-porphyrinylene nanorings as a porphyrin analogue of cycloparaphenylenes

Hua Wei Jiang, Takayuki Tanaka, Hirotaka Mori, Kyu Hyung Park, Dongho Kim, Atsuhiro Osuka

Department of Chemistry

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

77 Citations (Scopus)

Abstract

β-to-β Directly linked cyclic Ni(II) porphyrin trimer, tetramer, and pentamer ([3]CP, [4]CP, and [5]CP) have been synthesized by reaction of a 2,12-diborylated Ni(II) porphyrin with Pt(cod)Cl₂ followed by reductive elimination. The structures of these cyclic porphyrin arrays have been revealed by X-ray diffraction analysis. The strain energies of these cyclic oligomers are calculated to be 77, 57, and 47 kcal/mol for [3]CP, [4]CP, and [5]CP, respectively. Intramolecular excitation energy hopping was observed between the ³(d,d) states of the Ni(II) porphyrins with rates of 3.0, 4.4, and 4.6 ps for [3]CP, [4]CP, and [5]CP, respectively, reflecting the close proximity of the Ni(II) centers.

Original language	English
Pages (from-to)	2219-2222
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	6
DOIs	https://doi.org/10.1021/ja513102m
Publication status	Published - 2015 Feb 18

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Publisher Copyright:
© 2015 American Chemical Society.

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Cyclic 2,12-porphyrinylene nanorings as a porphyrin analogue of cycloparaphenylenes",

abstract = "β-to-β Directly linked cyclic Ni(II) porphyrin trimer, tetramer, and pentamer ([3]CP, [4]CP, and [5]CP) have been synthesized by reaction of a 2,12-diborylated Ni(II) porphyrin with Pt(cod)Cl2 followed by reductive elimination. The structures of these cyclic porphyrin arrays have been revealed by X-ray diffraction analysis. The strain energies of these cyclic oligomers are calculated to be 77, 57, and 47 kcal/mol for [3]CP, [4]CP, and [5]CP, respectively. Intramolecular excitation energy hopping was observed between the 3(d,d) states of the Ni(II) porphyrins with rates of 3.0, 4.4, and 4.6 ps for [3]CP, [4]CP, and [5]CP, respectively, reflecting the close proximity of the Ni(II) centers.",

author = "Jiang, {Hua Wei} and Takayuki Tanaka and Hirotaka Mori and Park, {Kyu Hyung} and Dongho Kim and Atsuhiro Osuka",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = feb,

day = "18",

doi = "10.1021/ja513102m",

language = "English",

volume = "137",

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T1 - Cyclic 2,12-porphyrinylene nanorings as a porphyrin analogue of cycloparaphenylenes

AU - Jiang, Hua Wei

AU - Tanaka, Takayuki

AU - Mori, Hirotaka

AU - Park, Kyu Hyung

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2015/2/18

Y1 - 2015/2/18

N2 - β-to-β Directly linked cyclic Ni(II) porphyrin trimer, tetramer, and pentamer ([3]CP, [4]CP, and [5]CP) have been synthesized by reaction of a 2,12-diborylated Ni(II) porphyrin with Pt(cod)Cl2 followed by reductive elimination. The structures of these cyclic porphyrin arrays have been revealed by X-ray diffraction analysis. The strain energies of these cyclic oligomers are calculated to be 77, 57, and 47 kcal/mol for [3]CP, [4]CP, and [5]CP, respectively. Intramolecular excitation energy hopping was observed between the 3(d,d) states of the Ni(II) porphyrins with rates of 3.0, 4.4, and 4.6 ps for [3]CP, [4]CP, and [5]CP, respectively, reflecting the close proximity of the Ni(II) centers.

AB - β-to-β Directly linked cyclic Ni(II) porphyrin trimer, tetramer, and pentamer ([3]CP, [4]CP, and [5]CP) have been synthesized by reaction of a 2,12-diborylated Ni(II) porphyrin with Pt(cod)Cl2 followed by reductive elimination. The structures of these cyclic porphyrin arrays have been revealed by X-ray diffraction analysis. The strain energies of these cyclic oligomers are calculated to be 77, 57, and 47 kcal/mol for [3]CP, [4]CP, and [5]CP, respectively. Intramolecular excitation energy hopping was observed between the 3(d,d) states of the Ni(II) porphyrins with rates of 3.0, 4.4, and 4.6 ps for [3]CP, [4]CP, and [5]CP, respectively, reflecting the close proximity of the Ni(II) centers.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 6

ER -

Cyclic 2,12-porphyrinylene nanorings as a porphyrin analogue of cycloparaphenylenes

Abstract

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