Near-infrared BODIPY dyes modulated with spirofluorene moieties

Toshiyuki Kowada; Shuhei Yamaguchi; Hiroki Fujinaga; Kouichi Ohe

doi:10.1016/j.tet.2011.02.073

Near-infrared BODIPY dyes modulated with spirofluorene moieties

Toshiyuki Kowada, Shuhei Yamaguchi, Hiroki Fujinaga, Kouichi Ohe

IMRAM - Division of Organic- and Biomaterials Research

Kyoto University

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

23 Citations (Scopus)

Abstract

New structurally constrained BODIPY dyes having electron-donating substituents were synthesized. As the key compounds for the construction of the BODIPY dyes, 1′H-spiro-[fluorene-9,4′-indeno[1,2-b]pyrrole] (sp-FIP) derivatives with electron-donating groups, such as OMe and NMe₂ at its 6′-position, were prepared using palladium-catalyzed intramolecular direct C-H arylation of a pyrrole moiety. The resulting BODIPY dyes showed bathochromic shift in absorption and fluorescence spectra in comparison to the unsubstituted analogs. Furthermore, pH-dependent reversible spectrum changes of the BODIPY dye were observed with the addition of trifluoroacetic acid (TFA) and subsequent addition of i-Pr₂NEt.

Original language	English
Pages (from-to)	3105-3110
Number of pages	6
Journal	Tetrahedron
Volume	67
Issue number	17
DOIs	https://doi.org/10.1016/j.tet.2011.02.073
Publication status	Published - 2011 Apr 29

Keywords

BODIPY dye
C-H arylation
Charge transfer
Fluorescence
Near-infrared

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title = "Near-infrared BODIPY dyes modulated with spirofluorene moieties",

abstract = "New structurally constrained BODIPY dyes having electron-donating substituents were synthesized. As the key compounds for the construction of the BODIPY dyes, 1′H-spiro-[fluorene-9,4′-indeno[1,2-b]pyrrole] (sp-FIP) derivatives with electron-donating groups, such as OMe and NMe2 at its 6′-position, were prepared using palladium-catalyzed intramolecular direct C-H arylation of a pyrrole moiety. The resulting BODIPY dyes showed bathochromic shift in absorption and fluorescence spectra in comparison to the unsubstituted analogs. Furthermore, pH-dependent reversible spectrum changes of the BODIPY dye were observed with the addition of trifluoroacetic acid (TFA) and subsequent addition of i-Pr2NEt.",

keywords = "BODIPY dye, C-H arylation, Charge transfer, Fluorescence, Near-infrared",

author = "Toshiyuki Kowada and Shuhei Yamaguchi and Hiroki Fujinaga and Kouichi Ohe",

note = "Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research (B) (Grant No. 22350087 ) from the Japan Society for the Promotion of Science (JSPS) . T.K. gratefully acknowledges the financial support by the Global COE Program {\textquoteleft}International Center for Integrated Research and Advanced Education in Materials Science{\textquoteright} (No. B-09) of MEXT, administrated by the JSPS . ",

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doi = "10.1016/j.tet.2011.02.073",

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AU - Kowada, Toshiyuki

AU - Yamaguchi, Shuhei

AU - Fujinaga, Hiroki

AU - Ohe, Kouichi

N1 - Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research (B) (Grant No. 22350087 ) from the Japan Society for the Promotion of Science (JSPS) . T.K. gratefully acknowledges the financial support by the Global COE Program ‘International Center for Integrated Research and Advanced Education in Materials Science’ (No. B-09) of MEXT, administrated by the JSPS .

PY - 2011/4/29

Y1 - 2011/4/29

N2 - New structurally constrained BODIPY dyes having electron-donating substituents were synthesized. As the key compounds for the construction of the BODIPY dyes, 1′H-spiro-[fluorene-9,4′-indeno[1,2-b]pyrrole] (sp-FIP) derivatives with electron-donating groups, such as OMe and NMe2 at its 6′-position, were prepared using palladium-catalyzed intramolecular direct C-H arylation of a pyrrole moiety. The resulting BODIPY dyes showed bathochromic shift in absorption and fluorescence spectra in comparison to the unsubstituted analogs. Furthermore, pH-dependent reversible spectrum changes of the BODIPY dye were observed with the addition of trifluoroacetic acid (TFA) and subsequent addition of i-Pr2NEt.

AB - New structurally constrained BODIPY dyes having electron-donating substituents were synthesized. As the key compounds for the construction of the BODIPY dyes, 1′H-spiro-[fluorene-9,4′-indeno[1,2-b]pyrrole] (sp-FIP) derivatives with electron-donating groups, such as OMe and NMe2 at its 6′-position, were prepared using palladium-catalyzed intramolecular direct C-H arylation of a pyrrole moiety. The resulting BODIPY dyes showed bathochromic shift in absorption and fluorescence spectra in comparison to the unsubstituted analogs. Furthermore, pH-dependent reversible spectrum changes of the BODIPY dye were observed with the addition of trifluoroacetic acid (TFA) and subsequent addition of i-Pr2NEt.

KW - BODIPY dye

KW - C-H arylation

KW - Charge transfer

KW - Fluorescence

KW - Near-infrared

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DO - 10.1016/j.tet.2011.02.073

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JO - Tetrahedron

JF - Tetrahedron

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Near-infrared BODIPY dyes modulated with spirofluorene moieties

Abstract

Keywords

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