The Synthesis and Photo-Induced Deprotection Reaction of Calix[4]resorcinarene Derivatives Containing t-Butyl Ester Moieties

Hiroto Kudo, Kouji Mitani, Tadatomi Nishikubo, Masaya Mitsuishi, Tokuji Miyashita

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    28 Citations (Scopus)

    Abstract

    The syntheses and photoinduced deprotection reactions of calix[4]resorcinarene derivatives with pendant t-butyl ester moieties were examined. Calix[4]resorcinarenes, 1a-1h, were prepared by the condensation reaction of resorcinol with certain aldehydes in the presence of hydrochloric acid as a catalyst in ethanol at 80 °C for 30 min in good yields. The substitution reaction of 1a-1h with t-butyl bromoacetate using cesium carbonate as a base and tetrabutylammmonium bromide (TBAB) as a phase transfer catalyst was performed to afford the corresponding calix[4]resorcinarene derivatives, 2a-2h with pendant t-butyl ester groups. It was found that 2a, 2e, 2f, 2g, and 2h had film forming properties. The photoinduced deprotection reaction of calixarene derivatives 2a, 2e, 2f, 2g, and 2h was examined in the presence of bis-[4-(diphenylsulfonio)phenyl] sulfide (DPSP) as a photoacid generator in the film state upon UV irradiation for 5 min followed by heating at 170 °C. It was found that the deprotection reaction of the t-butyl ester groups of 2a, 2e, 2f, 2g, and 2h proceeded smoothly to produce the corresponding calixarene derivatives, 3a, 3e, 3f, 3g, and 3h with carboxylic acid groups, quantitatively.

    Original languageEnglish
    Pages (from-to)819-826
    Number of pages8
    JournalBulletin of the Chemical Society of Japan
    Volume77
    Issue number4
    DOIs
    Publication statusPublished - 2004 Apr 1

    ASJC Scopus subject areas

    • Chemistry(all)

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