Self-photosensitized [2 + 2] cycloaddition for synthesis of high-energy-density fuels

Xie, Junjian; Zhang, Xiangwen; Shi, Chengxiang; Pan, Lun; Hou, Fang; Nie, Genkuo; Xie, Jiawei; Liu, Qing; Zou, Ji‐Jun

doi:10.1039/c9se00863b

Cited by 18 publications

(12 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Xie et al. also examined the self‐condensation of isophorone via UV‐induced [2+2]‐coupling [298] . Increasing the temperature to 150 °C without the addition of UV light resulted in no reaction as expected based on the Woodward‐Hoffmann rules [299] .…”

Section: Isophoronementioning

confidence: 95%

Bio‐Based Cycloalkanes: The Missing Link to High‐Performance Sustainable Jet Fuels

Muldoon

Harvey

2020

ChemSusChem

View full text Add to dashboard Cite

David Glueck, with an emphasis on the synthesis of P-stereogenic phosphine ligands for asymmetric catalysis. He is currently a National Research Council (NRC) postdoctoral fellow with Dr. Benjamin Harvey at the Naval Air Warfare Center Weapons Division (NAWCWD) in China Lake, CA, USA. His research interests include the synthesis of small molecules with applications in fuels, materials, and catalysis. Benjamin G. Harvey received his Ph.D. in inorganic chemistry from the University of Utah, USA, in 2005, studying with Professor Richard D. Ernst. He is now a Senior Research Chemist at the Naval Air Warfare Center, Weapons Division located in China Lake, CA. His current research focuses on the utilization of bio-based substrates for the preparation of advanced materials and the development of hybrid synthetic routes that combine chemical catalysis with synthetic biology. Specific interests include advanced alternative fuels for jet, missile, and rocket propulsion, bio-based high-temperature thermosetting resins, biocomposites, lubricants, and green solvents.

show abstract

Section: Isophoronementioning

confidence: 95%

Bio‐Based Cycloalkanes: The Missing Link to High‐Performance Sustainable Jet Fuels

Muldoon

Harvey

2020

ChemSusChem

View full text Add to dashboard Cite

show abstract

“…Cycloaddition reactions provide a versatile and straightforward approach to synthesize carbocyclic or heterocyclic organic compounds, which are present in the molecular structure of medicine, high-density aviation fuels, − and crystalline materials . Additionally, multiple chiral centers can be constructed in a one-step cycloaddition reaction, which are widely used in organic synthesis.…”

Section: Photocatalytic Cycloaddition Reactionmentioning

confidence: 99%

Heterogeneous Photocatalytic Organic Transformation Reactions Using Conjugated Polymers-Based Materials

et al. 2020

Self Cite

View full text Add to dashboard Cite

Photocatalytic heterogeneous organic transformation is considered as an efficient, clean atomic economy, and low-energy consumption strategy for organic synthesis. Conjugated polymers (CPs)-based materials have recently shown great potential for diverse photocatalytic applications because of their unique properties, such as structural designability, recyclability, high chemical stability, and low cost, and they have emerged as promising alternatives to traditional molecular or inorganic photocatalyst in photoredox reactions. Immense efforts have been made toward the construction of CPs-based materials for versatile photocatalytic chemical transformations. In this Review, we aim to summarize the recent progress in CPs-based photocatalysts for heterogeneous photocatalytic organic transformations including oxidation, reduction, coupling, and cycloaddition reaction. This Review discusses the influence of molecular, electronic, and channel structure of CPs-based materials on light absorption, charge separation, and mass transfer in different photocatalytic photoredox reactions. The regulated synthesis, mechanistic discussions, and future challenges for heterogeneous photocatalytic organic transformation in CPs-based materials systems are also considered. It is expected that this Review could not only deepen the comprehension of photocatalytic organic transformation but also open up inspirations and feasibilities for the applications of CPs-based materials.

show abstract

“…The cycloaddition mechanism of isophorone Reproduced with permission from Ref. [19]. Copyright 2020 Royal Society of Chemistry and β-pinene may involve a self-sensitized triplet energy transfer process, as shown in Fig.…”

Section: Spiro-fuelsmentioning

confidence: 99%

“…The same group then used biomass-derived ketenes (isophorone) and olefins (cyclohexene) as a reactant without extra photosensitizers or photocatalysts to prepare high-tension four-membered ring high-energy-density fuels via selfsensitized [2 + 2] cycloaddition (Fig. 2b) [19]. In this reaction, isophorone functions as both a sensitizer and reactant in the reaction; triplet isophorone is the key to initiating the photoreaction, and the large E T gap between the quencher and isophorone can enhance the efficiency of triplet energy transfer.…”

Section: Spiro-fuelsmentioning

confidence: 99%

Photocatalytic Synthesis of High-Energy-Density Fuel: Catalysts, Mechanisms, and Challenges

Xiao

Zhang

Pan

et al. 2021

Trans. Tianjin Univ.

Self Cite

View full text Add to dashboard Cite

High-energy-density liquid hydrocarbon fuels are generally synthesized using various chemical reactions to improve the performance (e.g., range, load, speed) of aerospace vehicles. Compared with conventional fuels, such as aviation kerosene and rocket kerosene, these liquid hydrocarbon fuels possess the advantages of high-energy-density and high volumetric calorific value; therefore, the fuels have important application value. The photocatalytic process has shown great potential for the synthesis of a diverse range of fuels on account of its unique properties, which include good efficiency, clean atomic economy, and low energy consumption. These characteristics have led to the emergence of the photocatalytic process as a promising complement and alternative to traditional thermocatalytic reactions for fuel synthesis. Extensive effort has been made toward the construction of catalysts for the multiple photocatalytic syntheses of high-energy-density fuels. In this review, we aim to summarize the research progress on the photocatalytic synthesis of high-energy-density fuel by using homogeneous and heterogeneous catalytic reactions. Specifically, the synthesis routes, catalysts, mechanistic features, and future challenges for the photocatalytic synthesis of high-energy-density fuel are described in detail. The highlights of this review not only promote the development of the photocatalytic synthesis of high-energy-density fuel but also expand the applications of photocatalysis to other fields. Graphic abstract

show abstract

Self-photosensitized [2 + 2] cycloaddition for synthesis of high-energy-density fuels

Abstract: High-energy-density fuels are synthesized through self-photosensitized [2 + 2] cycloaddition of isophorone and a wide range of olefins.

Cited by 18 publications

References 44 publications

Bio‐Based Cycloalkanes: The Missing Link to High‐Performance Sustainable Jet Fuels

Bio‐Based Cycloalkanes: The Missing Link to High‐Performance Sustainable Jet Fuels

Heterogeneous Photocatalytic Organic Transformation Reactions Using Conjugated Polymers-Based Materials

Photocatalytic Synthesis of High-Energy-Density Fuel: Catalysts, Mechanisms, and Challenges

Contact Info

Product

Resources

About