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<p>Elemental sulfur (S<sub>8</sub>), an abundant petroleum byproduct, is leveraged as a linchpin monomer in an organobase-catalyzed step-growth addition polymerization with dithiols and diacrylates at ambient temperature. This method enables the scalable synthesis of poly(ester disulfide)s—featuring alternating ester and disulfide linkages—with exceptional atom economy ( &gt; 95% yield), <i>M</i><sub>n</sub> up to 42.0 kDa, and dual functionality: biodegradable ester units and stimuli-responsive disulfides. Mechanistic studies reveal a chemoselective three-component coupling involving S<sub>8</sub> ring-opening, disulfide anion formation, and Michael addition, quantitatively generating symmetric and asymmetric disulfides in near-equimolar ratios. Thermal and mechanical characterizations of the poly(ester disulfide)s reveal programmable properties: High thermal stability (<i>T</i><sub>d,5%</sub> = 248–281 °C), tunable phase behavior (amorphous <i>T</i><sub>g</sub> = −64 °C to semicrystalline <i>T</i><sub>m</sub> = 142 °C), and reductive degradation. By overcoming traditional limitations of harsh conditions and monomer scope, this strategy establishes S<sub>8</sub> as a versatile feedstock for functional polymers, opening avenues for dynamic materials in biomedicine and environmental remediation.</p>

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Synthesis of poly(ester disulfide)s from S8-involved step-growth addition polymerization at ambient temperature

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年1月27日

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  • Yue Sun,
  • Yuxiang Cao,
  • Xiong Liu,
  • Chengjian Zhang,
  • Xinghong Zhang

摘要

Elemental sulfur (S8), an abundant petroleum byproduct, is leveraged as a linchpin monomer in an organobase-catalyzed step-growth addition polymerization with dithiols and diacrylates at ambient temperature. This method enables the scalable synthesis of poly(ester disulfide)s—featuring alternating ester and disulfide linkages—with exceptional atom economy ( > 95% yield), Mn up to 42.0 kDa, and dual functionality: biodegradable ester units and stimuli-responsive disulfides. Mechanistic studies reveal a chemoselective three-component coupling involving S8 ring-opening, disulfide anion formation, and Michael addition, quantitatively generating symmetric and asymmetric disulfides in near-equimolar ratios. Thermal and mechanical characterizations of the poly(ester disulfide)s reveal programmable properties: High thermal stability (Td,5% = 248–281 °C), tunable phase behavior (amorphous Tg = −64 °C to semicrystalline Tm = 142 °C), and reductive degradation. By overcoming traditional limitations of harsh conditions and monomer scope, this strategy establishes S8 as a versatile feedstock for functional polymers, opening avenues for dynamic materials in biomedicine and environmental remediation.