Transient-Ligand-Enabled ortho-Arylation of Five-Membered Heterocycles: Facile Access to Mechanochromic Materials
- 18 March 2018
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 57 (13), 3401-3405
- https://doi.org/10.1002/anie.201713357
Abstract
Reported herein is the first example of a direct arylation of heteroarenes by a transient-ligand-directed strategy without the need to construct and deconstruct the directing group. A wide range of heteroarenes undergoes the coupling with diverse aryl iodides to assemble a large library of highly selective and functionalized 3-arylthiophene-2-carbaldehydes. This route provides an opportunity to rapidly access new mechanofluorochromic materials. Moreover, a novel strategy for mechanochromic luminogens with chromism trends of red- and blue-shifts has been disclosed for the first time by facile functional-group modifications to a common structural core.Funding Information
- Division of Chemistry (CHE-1350541)
- Indo-US Science and Technology Forum (2016/66-K.S.)
This publication has 42 references indexed in Scilit:
- Cation–Anion Interaction‐Directed Molecular Design Strategy for Mechanochromic LuminescenceAdvanced Functional Materials, 2013
- Blue fluorescent emitters: design tactics and applications in organic light-emitting diodesChemical Society Reviews, 2013
- Recent advances in organic mechanofluorochromic materialsChemical Society Reviews, 2012
- Role of Molecular Packing in Determining Solid-State Optical Properties of π-Conjugated MaterialsThe Journal of Physical Chemistry Letters, 2011
- A General Catalyst for the β‐Selective C–H Bond Arylation of Thiophenes with IodoarenesAngewandte Chemie, 2010
- A General Catalyst for the β-Selective C-H Bond Arylation of Thiophenes with IodoarenesAngewandte Chemie, 2010
- Programmed Synthesis of Tetraarylthiophenes through Sequential C−H ArylationJournal of the American Chemical Society, 2009
- Reproducible on–off switching of solid-state luminescence by controlling molecular packing through heat-mode interconversionNature Materials, 2005
- The Role of Cystine Knots in Collagen Folding and Stability, Part II. Conformational Properties of (Pro‐Hyp‐Gly)n Model Trimers with N‐ and C‐Terminal Collagen Type III Cystine KnotsChemistry – A European Journal, 2003
- Development of the Traceless Phenylhydrazide Linker for Solid-Phase SynthesisChemistry – A European Journal, 2003