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)

doi:10.1021/acspolymersau.6c00025

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)

View original source ↗Read source document ↗Export metadata ↓

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 ).

Explore related subjects

36 MATERIALS SCIENCE 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY Characterization Energetic Metathesis Norbornene Polymers Synthesis

Keep this discovery

BibTeX RIS

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

Cite the original work for its findings. Save a collection to share your selection of sources.

Discover connections

36 MATERIALS SCIENCE subject 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY subject Characterization subject Energetic subject Metathesis subject Norbornene subject Polymers subject Synthesis subject

Connections use source metadata and explicit phrase matches, not verified experimental comparisons.

KEEP EXPLORING

Related reports

DOE OSTI2026

Comprehensive structural characterization of charged polymers involved in moisture-driven direct air capture

This study provides a comprehensive structural characterization of commercially available alkaline anion-exchange polymers (Fumasep FAA-3 and IRA 900) used in moisture-driven direct air capture (DAC) of carbon dioxide. Using X-ray diffraction, SAXS/WAXS, atomic force microscopy, FIB-SEM, and transmission electron microscopy, the authors identify nanoscale clustering, porosity, swelling behavior, and humidity-dependent structural changes that influence CO₂ adsorption and release. These findings establish structure–function relationships critical for designing more durable and energy-efficient DAC polymer materials.

36 MATERIALS SCIENCE↗

DOE OSTI2023

Review of Carbon Support Coordination Environments for Single Metal Atom Electrocatalysts (SACS)

This topical review focuses on the distinct role of carbon support coordination environment of single-atom catalysts (SACs) for electrocatalysis. The article begins with an overview of atomic coordination configurations in SACs, including a discussion of the advanced characterization techniques and simulation used for understanding the active sites. A summary of key electrocatalysis applications is then provided. These processes are oxygen reduction reaction (ORR), oxygen evolution reaction (OER), hydrogen evolution reaction (HER), nitrogen reduction reaction (NRR), and carbon dioxide reduction reaction (CO 2 RR). The review then shifts to modulation of the metal atom-carbon coordination environments, focusing on nitrogen and other non-metal coordination through modulation at the first coordination shell and modulation in the second and higher coordination shells. Representative case studies are provided, starting with the classic four-nitrogen-coordinated single metal atom (M$-$N 4 ) based SACs. Bimetallic coordination models including homo-paired and hetero-paired active sites are also discussed, being categorized as emerging approaches. The theme of the discussions is the correlation between synthesis methods for selective doping, the carbon structure–electron configuration changes associated with the doping, the analytical techniques used to ascertain these changes, and the resultant electrocatalysis performance. In conclusion, critical unanswered questions as well as promising underexplored research directions are identified.

36 MATERIALS SCIENCE↗

DOE OSTI2025

pi-Extended Porphyrins: The Impact of Aromatic Heterocycles on the Properties of the Largely pi-Extended Structures (Final Report_UNT_SC0016766)

Largely π-extended carbon-rich materials represent fascinating yet challenging frontiers in chemistry and materials science as it offers numerous opportunities in molecular electronics. pi-Extended porphyrins possess unique set of electronic and photophysical properties and are very attractive for a wide range of applications. However, the synthesis and functionalization of pi-extended porphyrins had been very challenging. To explore and expand this intriguing research field, it is essential to develop synthetic tools to make them accessible. Funded by the Department of Energy Basic Energy Science, my laboratory addressed these synthetic challenges by developing concise and versatile methods for pi-extended porphyrins. Significant progress has been made in multiple directions, including fusing Polycyclic Aromatic Hydrocarbons (PAH), aromatic heterocycles, antiaromatic component, and cross-conjugated component to porphyrins as well as push-pull porphyrins. The availability of these methods has made it possible to rationally design and synthesize functionalized pi-extended porphyrins. Unprecedented electronic and photophysical properties have been discovered for these pi-extended porphyrins.

36 MATERIALS SCIENCE↗