Expanded dipyrrins with electron-withdrawing substituents: Broad range of absorption in the visible region

Xu Liang; Soji Shimizu; Nagao Kobayashi

doi:10.1016/j.tetlet.2013.11.013

Expanded dipyrrins with electron-withdrawing substituents: Broad range of absorption in the visible region

Xu Liang, Soji Shimizu, Nagao Kobayashi

SCI - Chemistry

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

4 Citations (Scopus)

Abstract

Reaction of meso-aryl-substituted dipyrromethanes with tetracyanoethylene led to generation of a mono-tricyanovinyl-substituted species as well as an expanded dipyrrin analogue bearing both a dicyanomethylene and a tricyanovinyl substituent at the α-positions. These novel compounds exhibit absorption spectral features perturbed by the electron-withdrawing substituents. Unique protonation-induced spectral changes were also disclosed.

Original language	English
Pages (from-to)	256-258
Number of pages	3
Journal	Tetrahedron Letters
Volume	55
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2013.11.013
Publication status	Published - 2014 Jan 1

Keywords

Dipyrrin
Electronic absorption
Functional dyes
Push-pull effect

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.11.013

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title = "Expanded dipyrrins with electron-withdrawing substituents: Broad range of absorption in the visible region",

abstract = "Reaction of meso-aryl-substituted dipyrromethanes with tetracyanoethylene led to generation of a mono-tricyanovinyl-substituted species as well as an expanded dipyrrin analogue bearing both a dicyanomethylene and a tricyanovinyl substituent at the α-positions. These novel compounds exhibit absorption spectral features perturbed by the electron-withdrawing substituents. Unique protonation-induced spectral changes were also disclosed.",

keywords = "Dipyrrin, Electronic absorption, Functional dyes, Push-pull effect",

author = "Xu Liang and Soji Shimizu and Nagao Kobayashi",

note = "Funding Information: This work was partly supported by the Grant-in-Aids for Scientific Research (B) (No. 23350095 ) and (C) (No. 23550040 ) from JSPS, and a Grant-in-Aid for Scientific Research on Innovative Areas (No. 25109502 , {"}Stimuli-responsive Chemical Species{"}) from MEXT. The authors thank Professor Takeaki Iwamoto and Dr. Shintaro Ishida, Tohoku University for the X-ray measurements. ",

year = "2014",

month = jan,

day = "1",

doi = "10.1016/j.tetlet.2013.11.013",

language = "English",

volume = "55",

pages = "256--258",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "1",

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TY - JOUR

T1 - Expanded dipyrrins with electron-withdrawing substituents

T2 - Broad range of absorption in the visible region

AU - Liang, Xu

AU - Shimizu, Soji

AU - Kobayashi, Nagao

N1 - Funding Information: This work was partly supported by the Grant-in-Aids for Scientific Research (B) (No. 23350095 ) and (C) (No. 23550040 ) from JSPS, and a Grant-in-Aid for Scientific Research on Innovative Areas (No. 25109502 , "Stimuli-responsive Chemical Species") from MEXT. The authors thank Professor Takeaki Iwamoto and Dr. Shintaro Ishida, Tohoku University for the X-ray measurements.

PY - 2014/1/1

Y1 - 2014/1/1

N2 - Reaction of meso-aryl-substituted dipyrromethanes with tetracyanoethylene led to generation of a mono-tricyanovinyl-substituted species as well as an expanded dipyrrin analogue bearing both a dicyanomethylene and a tricyanovinyl substituent at the α-positions. These novel compounds exhibit absorption spectral features perturbed by the electron-withdrawing substituents. Unique protonation-induced spectral changes were also disclosed.

AB - Reaction of meso-aryl-substituted dipyrromethanes with tetracyanoethylene led to generation of a mono-tricyanovinyl-substituted species as well as an expanded dipyrrin analogue bearing both a dicyanomethylene and a tricyanovinyl substituent at the α-positions. These novel compounds exhibit absorption spectral features perturbed by the electron-withdrawing substituents. Unique protonation-induced spectral changes were also disclosed.

KW - Dipyrrin

KW - Electronic absorption

KW - Functional dyes

KW - Push-pull effect

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U2 - 10.1016/j.tetlet.2013.11.013

DO - 10.1016/j.tetlet.2013.11.013

M3 - Article

AN - SCOPUS:84890216385

SN - 0040-4039

VL - 55

SP - 256

EP - 258

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

Expanded dipyrrins with electron-withdrawing substituents: Broad range of absorption in the visible region

Abstract

Keywords

ASJC Scopus subject areas

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