Porphyrin Analogues of a Trityl Cation and Anion

Kenichi Kato, Woojae Kim, Dongho Kim, Hideki Yorimitsu, Atsuhiro Osuka

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Porphyrin-stabilized meso- or β-carbocations were generated upon treatment of the corresponding bis(4-tert-butylphenyl)porphyrinylcarbinols with trifluoroacetic acid (TFA). Bis(4-tert-butylphenyl)porphyrinylcarbinols were treated with TFA to generate the corresponding carbocations stabilized by a meso- or β-porphyrinyl group. The meso-porphyrinylmethyl carbocation displayed more effective charge delocalization with decreasing aromaticity compared with the β-porphyrinylmethyl carbocation. A propeller-like porphyrin trimer, tris(β-porphyrinyl)carbinol, was also synthesized and converted to the corresponding cation that displayed a more intensified absorption reaching over the NIR region. meso-Porphyrinylmethyl carbanion was generated as a stable species upon deprotonation of bis(4-tert-butylphenyl)(meso-porphyrinyl)methane with potassium bis(trimethylsilyl)amide (KHMDS) and [18]crown-6, whereas β-porphyrinylmethyl anions were highly unstable.

Original languageEnglish
Pages (from-to)7041-7045
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number21
DOIs
Publication statusPublished - 2016 May 17

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Trifluoroacetic acid
Trifluoroacetic Acid
Porphyrins
Anions
Cations
Negative ions
Positive ions
Deprotonation
Methane
Propellers
Amides
Methanol
Potassium
18-crown-6

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Kato, Kenichi ; Kim, Woojae ; Kim, Dongho ; Yorimitsu, Hideki ; Osuka, Atsuhiro. / Porphyrin Analogues of a Trityl Cation and Anion. In: Chemistry - A European Journal. 2016 ; Vol. 22, No. 21. pp. 7041-7045.
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abstract = "Porphyrin-stabilized meso- or β-carbocations were generated upon treatment of the corresponding bis(4-tert-butylphenyl)porphyrinylcarbinols with trifluoroacetic acid (TFA). Bis(4-tert-butylphenyl)porphyrinylcarbinols were treated with TFA to generate the corresponding carbocations stabilized by a meso- or β-porphyrinyl group. The meso-porphyrinylmethyl carbocation displayed more effective charge delocalization with decreasing aromaticity compared with the β-porphyrinylmethyl carbocation. A propeller-like porphyrin trimer, tris(β-porphyrinyl)carbinol, was also synthesized and converted to the corresponding cation that displayed a more intensified absorption reaching over the NIR region. meso-Porphyrinylmethyl carbanion was generated as a stable species upon deprotonation of bis(4-tert-butylphenyl)(meso-porphyrinyl)methane with potassium bis(trimethylsilyl)amide (KHMDS) and [18]crown-6, whereas β-porphyrinylmethyl anions were highly unstable.",
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Kato, K, Kim, W, Kim, D, Yorimitsu, H & Osuka, A 2016, 'Porphyrin Analogues of a Trityl Cation and Anion', Chemistry - A European Journal, vol. 22, no. 21, pp. 7041-7045. https://doi.org/10.1002/chem.201600473

Porphyrin Analogues of a Trityl Cation and Anion. / Kato, Kenichi; Kim, Woojae; Kim, Dongho; Yorimitsu, Hideki; Osuka, Atsuhiro.

In: Chemistry - A European Journal, Vol. 22, No. 21, 17.05.2016, p. 7041-7045.

Research output: Contribution to journalArticle

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