<b>Synthesis of Phenyleneethynylene Macrocycle Bearing Optically Active Amide Groups Undergoing Reversible Sol</b>−<b>Gel Transformation </b>

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  • Tatsuya Ogawa
    Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University
  • Taichi Sotani
    Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University
  • Yu Miyagi
    Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University
  • Fumio Sanda
    Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University

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Other Title
  • <b>可逆的ゾル－ゲル転移をする </b><b>光学活性アミド基含有ポリフェニレンエチニレンの合成 </b>
  • Synthesis of Phenyleneethynylene Macrocycle Bearing Optically Active Amide Groups Undergoing Reversible Sol-Gel Transformation

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Abstract

<p>Cyclic phenyleneethynylene 3 bearing optically active amide groups was synthesized by the Sonogashira−Hagihara coupling of ʟ-alanine-derived 3,5-dibromobenzamide 1 and 1,3-diethynylbenzene 2. The formation of 3 was confirmed by MALDI−TOF mass spectrometry along with 1H/13C-NMR and IR spectroscopies. A solution of 3 in CHCl3 turned into gelled state upon standing for 30 min, and the gel returned into fluid state by vibration. The sol−gel transformation was confirmed by dynamic viscoelastic measurement, wherein the storage modulus became larger than loss modulus around the angular frequency at 0.18 rad/s. A membrane of 3 fabricated by spin-coating on a quartz cell exhibited negative Cotton effects at 291 nm and 305 nm assignable to chirally assembled phenyleneethynylene moieties.</p>

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