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DOE OSTI · 3377273

The Synthesis and Ring-Opening Metathesis Polymerization of Energetic Norbornene Materials

Sterling, Valerie Ann [Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)] (ORCID:0000000253186174)·Davis, Jack Vickery [Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)] (ORCID:0000000236431721)·Tisdale, Jeremy Tyler [Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)] (ORCID:0000000172819021)·Chavez, David E. [Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)] (ORCID:000000024170320X)
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Abstract

Energetic norbornenes are promising candidates toward the development of new energetic polymers due to the synthetic versatility of norbornene ring-opening metathesis polymerizations used in commercial applications. We report the synthesis of two energetic norbornene materials that can be made in two steps with modest yields, containing either trinitroethanol or fluorodinitroethanol substituents. The norbornene monomers were then polymerized, and the polymers were characterized by Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), contact angle measurements, and proton and carbon nuclear magnetic resonance spectroscopies ( 1 H and 13 C{ 1 H} NMR). Additionally, small-scale safety data consisting of electrostatic discharge (ESD), friction (FS), and impact (IS) sensitivities were measured for the norbornene monomers and their resulting polymers. These analyses revealed that energetic norbornene materials are relatively insensitive and have densities comparable to that of TNT (1.47–1.81 g·cm –3 ).

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36 MATERIALS SCIENCE37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRYCharacterizationEnergeticMetathesisNorbornenePolymersSynthesis

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Sterling, Valerie Ann [Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)] (ORCID:0000000253186174), Davis, Jack Vickery [Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)] (ORCID:0000000236431721), Tisdale, Jeremy Tyler [Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)] (ORCID:0000000172819021), Chavez, David E. [Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)] (ORCID:000000024170320X). 2026-05-08. The Synthesis and Ring-Opening Metathesis Polymerization of Energetic Norbornene Materials. https://doi.org/10.1021/acspolymersau.6c00025

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36 MATERIALS SCIENCE subject37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY subjectCharacterization subjectEnergetic subjectMetathesis subjectNorbornene subjectPolymers subject

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