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2011•RSC AdvancesRequires access

Controlled Knoevenagel reactions of methyl groups of 1,3,5,7-tetramethyl BODIPY dyes for unique BODIPY dyes

Shilei Zhu, Jingtuo Zhang, Giri K. Vegesna, Ashutosh Tiwari, Fen‐Tair Luo, Mat­thias Zeller, Rudy L. Luck, Haihua Li, Sarah Green, Haiying Liu

Open publisher page 69 citations

Abstract

Formyl groups at 6- and 2,6-positions initiated Knoevenagel reactions of the methyl groups at the 7, and 1,7-positions of 1,3,5,7-tetramethyl BODIPY dyes with aromatic aldehydes. Formation of vinyl bonds at the 7-, and 1,7-positions facilitates further Knoevenagel reactions of the methyl groups at the 3,5-positions. This approach offers fast, facile and versatile ways to prepare potential novel building blocks of BODIPY dyes for conjugated oligomers, dendrimers, and highly water-soluble, near-infrared emissive sensing materials.

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What this paper is about

Formyl groups at 6- and 2,6-positions initiated Knoevenagel reactions of the methyl groups at the 7, and 1,7-positions of 1,3,5,7-tetramethyl BODIPY dyes with aromatic aldehydes. Formation of vinyl bonds at the 7-, and 1,7-positions facilitates further Knoevenagel reactions of the methyl groups at the 3,5-positions. This approach offers fast, facile and versatile ways to prepare potential novel building blocks of BODIPY dyes for conjugated oligomers, dendrimers, and highly water-soluble, near-infrared emissive sensing materials.

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OpenAlex reports 69 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

Formyl groups at 6- and 2,6-positions initiated Knoevenagel reactions of the methyl groups at the 7, and 1,7-positions of 1,3,5,7-tetramethyl BODIPY dyes with aromatic aldehydes. Formation of vinyl bonds at the 7-, and 1,7-positions facilitates further Knoevenagel reactions of the methyl groups at the 3,5-positions. This approach offers fast, facile and versatile ways to prepare potential novel building blocks of BODIPY dyes for conjugated oligomers, dendrimers, and highly water-soluble, near-infrared emissive sensing materials.

Key concepts: Knoevenagel condensation, BODIPY, Chemistry, Conjugated system, Photochemistry, Organic chemistry, Combinatorial chemistry, Fluorescence

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