Synthesis of liquid caged hydrocarbon fuel by intramolecular [2+2] photocycloaddition for advanced propulsion

Yumei Shu; Jinxiu Hu; Lin Yang; Tehreem Yaqub; Minhua Ai; Yang Liu; Dandan Shi; Kang Xue; Chengxiang Shi; Xiangwen Zhang; Jijun Zou; Lun Pan

doi:10.1016/j.cjche.2025.07.013

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Synthesis of liquid caged hydrocarbon fuel by intramolecular [2+2] photocycloaddition for advanced propulsion

Updated：2026-02-12

- Synthesis of liquid caged hydrocarbon fuel by intramolecular [2+2] photocycloaddition for advanced propulsion
- Chinese Journal of Chemical Engineering Vol. 88, Issue 12, Pages: 142-151(2025)
- Affiliations：
  
  1. Key Laboratory for Green Chemical Technology of the Ministry of Education, School of Chemical Engineering and Technology, National Industry-Education Platform for Energy Storage, Tianjin University,Tianjin,China,300072
  2. Haihe Laboratory of Sustainable Chemical Transformations,Tianjin,China,300192
  3. Qinghai Yanhu Industry Co., LTD, Geermu,China,816000
  4. School of Ecology and Environmental Science, Qinghai Institute of Technology,Xining,China,810016
- Author bio：
- Funds：
- DOI：10.1016/j.cjche.2025.07.013
  CLC：
- Published：2025
- Accepted：
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Yumei Shu, Jinxiu Hu, Lin Yang, Tehreem Yaqub, Minhua Ai, Yang Liu, Dandan Shi, Kang Xue, Chengxiang Shi, Xiangwen Zhang, Jijun Zou, Lun Pan. Synthesis of liquid caged hydrocarbon fuel by intramolecular [2+2] photocycloaddition for advanced propulsion[J]. Chinese Journal of Chemical Engineering, 2025, 88(12): 142-151.
DOI：

Yumei Shu, Jinxiu Hu, Lin Yang, Tehreem Yaqub, Minhua Ai, Yang Liu, Dandan Shi, Kang Xue, Chengxiang Shi, Xiangwen Zhang, Jijun Zou, Lun Pan. Synthesis of liquid caged hydrocarbon fuel by intramolecular [2+2] photocycloaddition for advanced propulsion[J]. Chinese Journal of Chemical Engineering, 2025, 88(12): 142-151. DOI： 10.1016/j.cjche.2025.07.013.

摘要

Abstract

Intramolecular [2 + 2

]

photocycloaddition is a reliable way to synthesize high-strained cyclobutyl-containing structures for high-value chemicals. Here we propose a photosensitized dimer of methyl cyclopentadiene (DMCPD) intramolecular [2 + 2

]

cycloaddition to synthesize an intriguing liquid caged fuel

namely 3

8-dimethylpentacyclic [5.3.0.0

4.8

]

decane (MPCD)

with two four-membered rings

four five-membered rings and two methyl branched chains. The reaction conditions are optimized to obtain a high DMCPD conversion of 80.95% as well as a high MPCD selectivity of 74.19%. Based on the quenching experiment and low-temperature phosphorescence test

intramolecular [2 + 2

]

photocycloaddition complies with the Dexter triplet-energy-transfer mechanism

which is essentially double electron exchange between excited photosensitizer and DMCPD. Through kinetic studies

the reaction order (

= 1) and the reaction kinetic equation related to light intensity and DMCPD concentration are obtained. MPCD has excellent physicochemical properties

with a high density of 0.964 g·cm

-3

high net heat of combustion of 42.63 MJ·kg

-1

relatively low kinetic viscosity of 25.03 mm

·s

-1

at (20 ℃)

and high specific impulse of 328.19 s.

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