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<p>A methacrylate-functionalized coumarin-benzoic acid monomer, 4-(7-(methacryloyloxy)-2-oxo-2&#xa0;H-chromen-3-yl)benzoic acid (FRP), was successfully synthesized and polymerized via free-radical polymerization initiated by AIBN (azobisisobutyronitrile) to afford a fluorescent polymethacrylate pendant coumarin-grafted (FRPP) polymer. The chemical structures of the coumarin precursor, monomer and polymer were confirmed by FTIR, NMR, and mass spectrometry. Optical study revealed strong blue fluorescence from FRPP (<i>λex</i> = 386&#xa0;nm) with an enhanced relative quantum yield (<i>Φ</i> = 0.81) of polymer, determined using 7HCPC as an internal reference and compared with the monomer (<i>Φ</i> = 0.19), which is consistent with reduced non-radiative relaxation within the polymer matrix. UV-visible Tauc analysis gave optical band-gap values of 3.25&#xa0;eV for 7HCPC, 3.15&#xa0;eV for FRP, and 3.61&#xa0;eV for FRPP, showing that polymerization slightly modified the optical transition behaviour. X-ray diffraction analysis indicated a transition from the semicrystalline monomer to an amorphous polymer after polymerization. Thermal analysis revealed improved thermal transition of FRPP, including a glass transition temperature of 75.8&#xa0;°C and delayed thermal degradation and increases char yield relative to FRP. In addition, FRPP retained measurable antimicrobial activity as demonstrated by zone-of-inhibition assays at 250&#xa0;µg/mL. Covalent immobilization of the coumarin-benzoic acid chromophore does not eliminate bioactivity. These findings link molecular design, fluorescence activity, thermal stability and notable antimicrobial properties protected by pendant coumarin-grafted polymethacrylate FRPP polymer and underscore its potential as a platform for functional polymer development.</p> Graphical abstract <p></p>

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Structural and thermal behaviour of a fluorescent pendant coumarin-grafted polymethacrylate

  • 期刊论文

  • 发表日期：

    2026年8月4日

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  • Reena Hirani,
  • Shreyansh Mevada,
  • Karan Kamle,
  • Nishith Gamit,
  • Rutvik Patel,
  • Navinchandra Shimpi,
  • Dilip Vasava

摘要

A methacrylate-functionalized coumarin-benzoic acid monomer, 4-(7-(methacryloyloxy)-2-oxo-2 H-chromen-3-yl)benzoic acid (FRP), was successfully synthesized and polymerized via free-radical polymerization initiated by AIBN (azobisisobutyronitrile) to afford a fluorescent polymethacrylate pendant coumarin-grafted (FRPP) polymer. The chemical structures of the coumarin precursor, monomer and polymer were confirmed by FTIR, NMR, and mass spectrometry. Optical study revealed strong blue fluorescence from FRPP (λex = 386 nm) with an enhanced relative quantum yield (Φ = 0.81) of polymer, determined using 7HCPC as an internal reference and compared with the monomer (Φ = 0.19), which is consistent with reduced non-radiative relaxation within the polymer matrix. UV-visible Tauc analysis gave optical band-gap values of 3.25 eV for 7HCPC, 3.15 eV for FRP, and 3.61 eV for FRPP, showing that polymerization slightly modified the optical transition behaviour. X-ray diffraction analysis indicated a transition from the semicrystalline monomer to an amorphous polymer after polymerization. Thermal analysis revealed improved thermal transition of FRPP, including a glass transition temperature of 75.8 °C and delayed thermal degradation and increases char yield relative to FRP. In addition, FRPP retained measurable antimicrobial activity as demonstrated by zone-of-inhibition assays at 250 µg/mL. Covalent immobilization of the coumarin-benzoic acid chromophore does not eliminate bioactivity. These findings link molecular design, fluorescence activity, thermal stability and notable antimicrobial properties protected by pendant coumarin-grafted polymethacrylate FRPP polymer and underscore its potential as a platform for functional polymer development.

Graphical abstract