Soft and Rigid Imide-based Benzoxazines as Precursors to High-performance Polybenzoxazines: Synthesis, Thermal Behavior, and Tunable Photoluminescent Properties

Abdulsalam Mahdy; Jalal A. Zahra; Hassan K. Juwhari; Ruba I. Alzubi; Osama Younis

doi:10.1007/s10118-026-3833-0

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Soft and Rigid Imide-based Benzoxazines as Precursors to High-performance Polybenzoxazines: Synthesis, Thermal Behavior, and Tunable Photoluminescent Properties

RESEARCH ARTICLE | Updated：2026-09-28

- Soft and Rigid Imide-based Benzoxazines as Precursors to High-performance Polybenzoxazines: Synthesis, Thermal Behavior, and Tunable Photoluminescent Properties
- Chinese Journal of Polymer Science Vol. 44, Pages: 1-23(2026)
- Affiliations：
  
  a.Chemistry Department, School of Science, The University of Jordan, Amman 11942, Jordan
  b.Chemistry Department, Faculty of Education & Science, Rada’a, Albaydha University, Albaydha, Yemen
  c.Department of Pharmacy, Faculty of Medicine and Health Sciences, Ar-Rasheed Smart University, Sana’a, Yemen
  d.Department of Physics, School of Science, The University of Jordan, Amman 11942, Jordan
  e.Jordan Atomic Energy Commission, Amman 11934, Jordan
  f.Chemistry Department, Faculty of Science, New Valley University, El-Kharga 72511, Egypt
  g.Polymer Institute, Slovak Academy of Sciences, Dúbravská cesta 9, 84541, Bratislava, Slovakia
- Author bio：
  
  abdualsalam735@gmail.com, abdualsalamaljbri@baydaauniv.net (A.M.)
  osamayounis@sci.nvu.edu.eg (O.Y.)
- Funds：
- DOI：10.1007/s10118-026-3833-0
  CLC：
- Received：16 July 2026，
  
  Accepted：04 August 2026，
  
  Online First：28 September 2026，
  
  Published：2026-09
- Accepted：
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Mahdy, A.; Zahra, J. A.; Juwhari, H. K.; Alzubi, R. I.; Younis, O. Soft and rigid imide-based benzoxazines as precursors to high-performance polybenzoxazines: synthesis, thermal behavior, and tunable photoluminescent properties. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-026-3833-0

Abdulsalam Mahdy, Jalal A. Zahra, Hassan K. Juwhari, et al. Soft and Rigid Imide-based Benzoxazines as Precursors to High-performance Polybenzoxazines: Synthesis, Thermal Behavior, and Tunable Photoluminescent Properties[J/OL]. Chinese Journal of Polymer Science, 2026, 441-23.
Mahdy, A.; Zahra, J. A.; Juwhari, H. K.; Alzubi, R. I.; Younis, O. Soft and rigid imide-based benzoxazines as precursors to high-performance polybenzoxazines: synthesis, thermal behavior, and tunable photoluminescent properties. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-026-3833-0 DOI：

Abdulsalam Mahdy, Jalal A. Zahra, Hassan K. Juwhari, et al. Soft and Rigid Imide-based Benzoxazines as Precursors to High-performance Polybenzoxazines: Synthesis, Thermal Behavior, and Tunable Photoluminescent Properties[J/OL]. Chinese Journal of Polymer Science, 2026, 441-23. DOI： 10.1007/s10118-026-3833-0.

摘要

Abstract

Two new imide-functional benzoxazine monomers

IBZ-EDA

and

IBZ-PHDA

with distinct molecular architectures

were synthesized

via

a one-pot Mannich condensation reaction using ortho-phthalimide-functional phenol

paraformaldehyde

and either ethylenediamine or

para-

phenylenediamine as flexible and rigid bridging units

respectively. The chemical structures of the synthesized monomers were confirmed by Fourier transform infrared spectroscopy (FTIR)

proton nuclear magnetic resonance spectroscopy (

H-NMR)

Carbon-13 (

C)-NMR

distortionless enhancement by polarization transfer (DEPT-135)

correlation spectroscopy (COSY)

heteronuclear single quantum coherence (HSQC)

heteronuclear multiple bond correlation (HMBC)

and mass spectrometry analyses. Thermal ring-opening polymerization of the monomers produced highly crosslinked polybenzoxazine networks

Poly(IBZ-EDA)

and

Poly(IBZ-PHDA)

whose curing behaviors were investigated using DSC and FTIR. The flexible

IBZ-EDA

monomer exhibited a lower polymerization temperature owing to the proximity of the oxazine rings and favorable intramolecular interactions

whereas the rigid aromatic

IBZ-PHDA

structure required a higher curing temperature. Thermogravimetric analysis demonstrated substantial improvements in thermal stability after curing

with

Poly(IBZ-PHDA)

exhibiting outstanding performance

including

values up to 559 °C

a char yield of 79%

and a limiting oxygen index of 49.1%

reflecting its highly flame-retardant nature. Scanning electron microscopy (SEM) analysis revealed dense and highly crosslinked morphologies with structural differences arising from

the flexibility of the diamine spacer. Photophysical investigations in the solution and solid states revealed complex excitation-dependent fluorescence behaviors for both monomers and polymers. The emission properties were strongly influenced by concentration

excitation wavelength

molecular packing

and polymer network formation. Dual-emission characteristics

broad chromaticity tunability

and multiple emissive states are observed

indicating the coexistence of locally excited

aggregated

and cluster-associated emissive species. Polymerization further alters the excited-state landscape through enhanced intermolecular interactions and restricted molecular motion. The results demonstrate that linker rigidity plays a critical role in controlling both the thermal and photophysical properties

providing an effective strategy for designing multifunctional polybenzoxazines with exceptional thermal stability

flame retardancy

and tunable luminescence.

关键词

Keywords

references

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