Benzophenone as a cheap and effective photosensitizer for the photocatalytic synthesis of dimethyl cubane-1,4-dicarboxylate

Callum Prentice; Alice Elizabeth Martin; J. James Morrison; Andrew D. Smith; Eli Zysman-Colman

doi:10.1039/D3OB00231D

Benzophenone as a cheap and effective photosensitizer for the photocatalytic synthesis of dimethyl cubane-1,4-dicarboxylate

Callum Prentice, Alice Elizabeth Martin, J. James Morrison, Andrew D. Smith^*, Eli Zysman-Colman^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

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Abstract

The key intramolecular [2 + 2] photochemical cycloaddition step in the synthesis of dimethyl cubane-1,4-dicarboxylate is performed with substoichiometric amounts of the photosensitizer benzophenone. The reaction proceeds via a Dexter energy transfer process between the triplet excited state benzophenone and a well-known cubane precursor diene. The use of the cheap and widely available benzophenone as the photosensitizer enables lower energy light to be used than the traditional photochemical process.

Original language	English
Pages (from-to)	3307-3310
Number of pages	4
Journal	Organic & Biomolecular Chemistry
Volume	21
Issue number	16
Early online date	20 Feb 2023
DOIs	https://doi.org/10.1039/D3OB00231D
Publication status	Published - 28 Apr 2023

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10.1039/D3OB00231DLicence: CC BY

Prentice_2023_OBC_Benzophenone_CC
Copyright © 2023 The Author(s). Open Access. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Final published version, 512 KBLicence: CC BY

Benzophenone as a Cheap and Effective Photosensitizer for the Photocatalytic Synthesis of Dimethyl Cubane-1,4-dicarboxylate (dataset)
Prentice, C. (Creator), Martin, A. E. (Creator), Morrison, J. J. (Creator), Smith, A. D. (Creator) & Zysman-Colman, E. (Creator), University of St Andrews, 24 Feb 2023
DOI: 10.17630/e66ca579-375d-40f1-85fc-caaec4985476
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title = "Benzophenone as a cheap and effective photosensitizer for the photocatalytic synthesis of dimethyl cubane-1,4-dicarboxylate",

abstract = "The key intramolecular [2 + 2] photochemical cycloaddition step in the synthesis of dimethyl cubane-1,4-dicarboxylate is performed with substoichiometric amounts of the photosensitizer benzophenone. The reaction proceeds via a Dexter energy transfer process between the triplet excited state benzophenone and a well-known cubane precursor diene. The use of the cheap and widely available benzophenone as the photosensitizer enables lower energy light to be used than the traditional photochemical process.",

author = "Callum Prentice and Martin, {Alice Elizabeth} and Morrison, {J. James} and Smith, {Andrew D.} and Eli Zysman-Colman",

note = "The authors thank AstraZeneca and the University of St Andrews for funding (CASE studentship C.P.).",

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doi = "10.1039/D3OB00231D",

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T1 - Benzophenone as a cheap and effective photosensitizer for the photocatalytic synthesis of dimethyl cubane-1,4-dicarboxylate

AU - Prentice, Callum

AU - Martin, Alice Elizabeth

AU - Morrison, J. James

AU - Smith, Andrew D.

AU - Zysman-Colman, Eli

N1 - The authors thank AstraZeneca and the University of St Andrews for funding (CASE studentship C.P.).

PY - 2023/4/28

Y1 - 2023/4/28

N2 - The key intramolecular [2 + 2] photochemical cycloaddition step in the synthesis of dimethyl cubane-1,4-dicarboxylate is performed with substoichiometric amounts of the photosensitizer benzophenone. The reaction proceeds via a Dexter energy transfer process between the triplet excited state benzophenone and a well-known cubane precursor diene. The use of the cheap and widely available benzophenone as the photosensitizer enables lower energy light to be used than the traditional photochemical process.

AB - The key intramolecular [2 + 2] photochemical cycloaddition step in the synthesis of dimethyl cubane-1,4-dicarboxylate is performed with substoichiometric amounts of the photosensitizer benzophenone. The reaction proceeds via a Dexter energy transfer process between the triplet excited state benzophenone and a well-known cubane precursor diene. The use of the cheap and widely available benzophenone as the photosensitizer enables lower energy light to be used than the traditional photochemical process.

U2 - 10.1039/D3OB00231D

DO - 10.1039/D3OB00231D

M3 - Article

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VL - 21

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EP - 3310

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 16

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Benzophenone as a cheap and effective photosensitizer for the photocatalytic synthesis of dimethyl cubane-1,4-dicarboxylate

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Benzophenone as a Cheap and Effective Photosensitizer for the Photocatalytic Synthesis of Dimethyl Cubane-1,4-dicarboxylate (dataset)

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