Issue 36, 2015

Meso enyne substituted BODIPYs: synthesis, structure and properties

Abstract

We report the synthesis of meso enyne substituted BODIPYs by the reaction of 8-chloro BODIPY with terminal alkynes under Sonogashira coupling conditions, and by Pd–Cu catalyzed hydroalkynylation reaction of terminal alkynes, across the –C[triple bond, length as m-dash]C– bond of meso alkynylated BODIPYs. The scope of reaction was explored by reacting different meso alkynylated BODIPYs with various terminal alkynes, which results in meso enyne substituted BODIPYs with different substituents. The meso enyne substituted BODIPYs show blue shifted absorption and red shifted emission with large Stokes shift compared to meso alkynylated BODIPYs. The single crystal structures of BODIPYs 2a, 3b, 4a and 2d are reported. Their packing diagram exhibits extensive intermolecular C–H⋯π, C–H⋯F hydrogen bonding and π⋯π stacking interactions, leading to 1D supramolecular frameworks extending into the complex 3D structural frameworks.

Graphical abstract: Meso enyne substituted BODIPYs: synthesis, structure and properties

Supplementary files

Article information

Article type
Paper
Submitted
07 Feb 2015
Accepted
13 Mar 2015
First published
16 Mar 2015

Dalton Trans., 2015,44, 15803-15812

Author version available

Meso enyne substituted BODIPYs: synthesis, structure and properties

B. Dhokale, T. Jadhav, S. M. Mobin and R. Misra, Dalton Trans., 2015, 44, 15803 DOI: 10.1039/C5DT00565E

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