meso-(4-(N,N-dialkylamino)phenyl)-substituted subporphyrins: Remarkably perturbed absorption spectra and enhanced fluorescence by intramolecular charge transfer interactions

Yasuhide Inokuma, Shanmugam Easwaramoorthi, Seok Yoon Zin, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

A series of meso-(4-(N,N-dibenzylamino)phenyl)-substituted subporphyrins was synthesized by means of Buchwald-Hartwig amination protocol. Substitution of the amino group at the 4-position of the meso-phenyl substituent resulted in a remarkable red shift in the absorption spectra and drastic enhancement of fluorescence intensity probably as a consequence of intramolecular CT interaction. These characteristics have been utilized to construct a cation-sensing system by appending a 1-aza-15-crown-5 unit to subporphyrin that displays large spectral changes upon cation binding.

Original languageEnglish
Pages (from-to)12234-12235
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number37
DOIs
Publication statusPublished - 2008 Sep 17

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Cations
Charge transfer
Absorption spectra
Fluorescence
Positive ions
Amination
Substitution reactions
15-crown-5

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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abstract = "A series of meso-(4-(N,N-dibenzylamino)phenyl)-substituted subporphyrins was synthesized by means of Buchwald-Hartwig amination protocol. Substitution of the amino group at the 4-position of the meso-phenyl substituent resulted in a remarkable red shift in the absorption spectra and drastic enhancement of fluorescence intensity probably as a consequence of intramolecular CT interaction. These characteristics have been utilized to construct a cation-sensing system by appending a 1-aza-15-crown-5 unit to subporphyrin that displays large spectral changes upon cation binding.",
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meso-(4-(N,N-dialkylamino)phenyl)-substituted subporphyrins : Remarkably perturbed absorption spectra and enhanced fluorescence by intramolecular charge transfer interactions. / Inokuma, Yasuhide; Easwaramoorthi, Shanmugam; Zin, Seok Yoon; Kim, Dongho; Osuka, Atsuhiro.

In: Journal of the American Chemical Society, Vol. 130, No. 37, 17.09.2008, p. 12234-12235.

Research output: Contribution to journalArticle

TY - JOUR

T1 - meso-(4-(N,N-dialkylamino)phenyl)-substituted subporphyrins

T2 - Remarkably perturbed absorption spectra and enhanced fluorescence by intramolecular charge transfer interactions

AU - Inokuma, Yasuhide

AU - Easwaramoorthi, Shanmugam

AU - Zin, Seok Yoon

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2008/9/17

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AB - A series of meso-(4-(N,N-dibenzylamino)phenyl)-substituted subporphyrins was synthesized by means of Buchwald-Hartwig amination protocol. Substitution of the amino group at the 4-position of the meso-phenyl substituent resulted in a remarkable red shift in the absorption spectra and drastic enhancement of fluorescence intensity probably as a consequence of intramolecular CT interaction. These characteristics have been utilized to construct a cation-sensing system by appending a 1-aza-15-crown-5 unit to subporphyrin that displays large spectral changes upon cation binding.

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