NDLI: Iridium-catalyzed polymerization of benzoic acids and internal diynes: a new route for constructing high molecular weight polynaphthalenes without the constraint of monomer stoichiometry

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Iridium-catalyzed polymerization of benzoic acids and internal diynes: a new route for constructing high molecular weight polynaphthalenes without the constraint of monomer stoichiometry

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Polymer Chemistry Vol - 8 Issue - 7

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Iridium-catalyzed polymerization of benzoic acids and internal diynes: a new route for constructing high molecular weight polynaphthalenes without the constraint of monomer stoichiometry

Content Provider	Royal Society of Chemistry (RSC)
Author	Deng, Haiqin Lam, Jacky W. Y. Han, Ting Kwok, Ryan T. K. Zhao, Zheng Tang, Ben Zhong
Copyright Year	2017
Abstract	The development of new polymerization reactions conducted under monomer non-stoichiometric conditions has great academic and industrial significance. Herein we report such a new route for synthesizing functional polynaphthalenes (PNs). The polycoupling reactions of benzoic acid and its derivatives (1) with 4,4′-(1,6-hexylenedioxy)bis(diphenylacetylene) (2) proceed smoothly in o-xylene in the presence of [Cp*IrCl2]2 and Ag2CO3 at 140 °C, generating multisubstituted PNs with high molecular weights (Mw up to 228 700) in high yields (up to 98%). The effect of monomer stoichiometry on the polymerization was systematically investigated and the best result was obtained at a molar feed ratio of 1 : 2 of 2 : 1. The associated mechanism for the monomer non-stoichiometry enhancement effect was proposed. All the obtained PNs show good thermal stability and excellent optical transparency. They possess good film-forming ability and their thin films exhibit high refractive indices (n = 1.7653–1.6354). Polymers constructed from non-emissive monomers show light emission in solutions due to the generation of fluorophores in situ during the polymerization. The polymer carrying a tetraphenylethene motif is weakly emissive in solution but emits intensely when aggregated, demonstrating a phenomenon of aggregation-induced emission. The efficient solid-state emission and good photosensitivity enable it to be utilized as a material for fabricating two-dimensional fluorescent photopatterns by irradiating its thin films under UV light through copper masks.
Starting Page	1393
Ending Page	1403
Page Count	11
File Format	HTM / HTML PDF
ISSN	17599954
Volume Number	8
Issue Number	8
Journal	Polymer Chemistry
DOI	10.1039/c6py02165d
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Stoichiometry Photosensitivity Molar mass Refractive index Silver carbonate Polymerization Polymer Diphenylacetylene O-Xylene Non-stoichiometric compound Molar mass distribution Monomer Copper
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Bioengineering Biomedical Engineering Polymers and Plastics

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