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

Shilei Zhu; Jingtuo Zhang; Giri Vegesna; Ashutosh Tiwari; Fen-Tair Luo; Matthias Zeller; Rudy Luck; Haihua Li; Sarah Green; Haiying Liu

doi:10.1039/C1RA00678A

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

Shilei Zhu,^a Jingtuo Zhang,^a Giri Vegesna,^a Ashutosh Tiwari,^a Fen-Tair Luo,^b Matthias Zeller,^c Rudy Luck,^a Haihua Li,^d Sarah Green^a and Haiying Liu*^a

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* Corresponding authors

^a Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI, USA
E-mail: hyliu@mtu.edu
Fax: +1 9064872061
Tel: +1 9064873451

^b Institute of Chemistry, Academia Sinica, Taipei, Taiwan, Republic of China

^c Department of Chemistry, Youngstown State University, Youngstown, OH, USA

^d University Libraries, University of Alabama, Tuscaloosa, AL, USA

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.

This article is part of the themed collection: Organic Collection: from theory to synthesis, from molecules to materials, catalysis and beyond

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

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

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