Synthesis and Solid-State Polymerization of Butadiyne Derivatives with Trialkoxyphenylurethane Groups

Abstract

3,4,5-Trialkoxyphenyl isocyanate derivatives, in which alkoxy was dodecyloxy or methoxy, reacted with 4,6-decadiyn-1,10-diol and 5,7-dodecadiyn-1,12-diol, and four butadiyne derivatives with (N-trialkoxyphenyl)urethane groups were successfully synthesized. Their solid-state polymerization stimulated by UV or γ-ray irradiation was investigated. All monomers in crystals were found to be polymerizable. However, conversion was different depending on the compounds. The derivatives from 5,7-dodecadiyn-1,12-diol showed better conversion, suggesting that they have more favorable monomer arrangement for the solid-state polymerization. Polymers of dodecyloxy derivatives could be partially dissolved in chloroform and they showed solvatochromism when hexane was added to the solution. As was expected from the structure of tridodecyloxyphenyl groups introduced, dodecyloxy derivatives gave organogels in various organic solvents in the concentration less than 2 wt %. However, these gels could not be polymerized by UV irradiation, and the monomer alignment was found to be different between crystalline and gel states.

Functional π-Gelators and Their Applications

“…UV irradiation of the hydrogel derived helical ribbons of 87 (Chart ) at 254 nm resulted in the polymerization of self-assembled gelators leading to a red coloration . Stimuli responsive polydiacetylenes were prepared by the cross-linking of the diacetylene-containing glycolipids 88 – 90 (Chart ). , The diacetylene amide derivatives 91 – 93 (Figure ) form gels which upon UV irradiation undergo polymerization. − Interesingly, the gelators 93a – f , exhibited odd–even effect on the color of the polymer obtained . The odd–even effect in the carbon atoms of the aliphatic chains controls the planarity of the polymers and hence the color of the odd chain gels is red and that of the even chain is blue (Figure ).…”

Chemical composition, antioxidant and bioactivities of essential oils from Melaleuca bracteata leaves

“…Methyl eugenol was the main component of the M. bracteata EO, although the amount (66.68%) was slightly lower than previously reported (Almarie et al 2016;Cosgrove et al 1948;Hou et al 2016;Siddique et al 2017;Ye et al 2014;Zhong et al 2009). https://doi.org/10.17221/38/2019-PPS Methyl eugenol has been found in 450 different kinds of plants from 80 families, especially in spices and medicinal plants, and has extensive applications (Takahashi et al 2012). 3,4,5-Trimethoxy-benzoic acid methyl ester is used as a key intermediate to synthesise medicines to treat stomach pain, heart disease and anxiety (Godfrey et al 2013).…”

Benzoic hydroxamate-based iron complexes as model compounds for humic substances: synthesis, characterization and algal growth experiments

“…3,4,5-Trimethoxybenzhydroxamic acid 4a was synthesized according to the previously published procedure by reaction of 3,4,5-trimethoxybenzoic acid with thionyl chloride and subsequent conversion with hydroxylamine hydrochloride under alkaline conditions. 62 The Fe(III) complexes were synthesized by deprotonation of the ligand with potassium hydroxide and addition of iron chloride in aqueous or methanolic solution (Scheme 2).…”