Journal of the American Chemical Society, volume 139, issue 44, pages 15812-15820

Wavelength Dependence of Light-Induced Cycloadditions

Jan P Menzel ^{1, 2}

Benjamin T. Noble ³

Andrea Lauer ^{1, 2, 4}

Michelle L. Coote ³

James P. Blinco ¹

Christopher Barner‐Kowollik ^{1, 2, 4}

Hide authors affiliations Show authors affiliations: 4 affiliations

School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology (QUT), 2 George Street, Brisbane, QLD 4000, Australia |

Macromolecular Architectures, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76131 Karlsruhe, Germany |

Australian Research Council Centre of Excellence for Electromaterials Science, Research School of Chemistry, Australian National University, Canberra, ACT 2601, Australia

Australian National University

Australian Research Council

Australian Research Council Centre of Excellence for Electromaterials Science

⁴

Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany |

Publication type: Journal Article

Publication date: 2017-10-25

American Chemical Society (ACS)

Journal: Journal of the American Chemical Society

Quartile SCImago

Quartile WOS

Impact factor: 15

ISSN: 00027863, 15205126

DOI: 10.1021/jacs.7b08047

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General Chemistry

Catalysis

Biochemistry

Colloid and Surface Chemistry

Abstract

The wavelength-dependent conversion of two rapid photoinduced ligation reactions, i.e., the light activation of o-methylbenzaldehydes, leading to the formation of reactive o-quinodimethanes (photoenols), and the photolysis of 2,5-diphenyltetrazoles, affording highly reactive nitrile imines, is probed via a monochromatic wavelength scan at constant photon count. The transient species are trapped by cycloaddition with N-ethylmaleimide, and the reactions are traced by high resolution mass spectrometry and nuclear magnetic resonance spectroscopy. The resulting action plots are assessed in the context of Beer-Lambert's law and provide combined with time-dependent density functional theory and multireference calculations an in-depth understanding of the underpinning mechanistic processes, including conical intersections. The π → π* transition of the carbonyl group of the o-methylbenzaldehyde correlates with a highly efficient conversion to the cycloadduct, showing no significant wavelength dependence, while conversion following the n → π* transition proceeds markedly less efficient at longer wavelengths. The influence of absorbance and reactivity has critical consequences for an effective reaction design: At high concentrations of o-methylbenzaldehydes (c = 8 mmol L-1), photoligations with N-ethylmaleimide (possible for λ ≤ 390 nm) are ideally performed at 330 nm, whereas at high light penetration regimes at lower concentrations (c = 0.3 mmol L-1), 315 nm irradiation leads to the highest conversion. Activation and trapping of 2,5-diphenyltetrazoles (possible for λ ≤ 322 nm) proceeds best at a wavelength shorter than 295 nm, irrespective of concentration.

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Citations by journals

	1 2 3 4 5 6 7 8 9
Journal of the American Chemical Society	Journal of the American Chemical Society, 9, 11.39% Journal of the American Chemical Society 9 publications, 11.39%
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Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 5, 6.33% Angewandte Chemie - International Edition 5 publications, 6.33%
Chemistry - A European Journal	Chemistry - A European Journal, 4, 5.06% Chemistry - A European Journal 4 publications, 5.06%
Advanced Materials	Advanced Materials, 4, 5.06% Advanced Materials 4 publications, 5.06%
Chemical Communications	Chemical Communications, 3, 3.8% Chemical Communications 3 publications, 3.8%
Nature Communications	Nature Communications, 2, 2.53% Nature Communications 2 publications, 2.53%
Advanced Functional Materials	Advanced Functional Materials, 2, 2.53% Advanced Functional Materials 2 publications, 2.53%
Macromolecules	Macromolecules, 2, 2.53% Macromolecules 2 publications, 2.53%
Chemical Reviews	Chemical Reviews, 2, 2.53% Chemical Reviews 2 publications, 2.53%
Journal of Organic Chemistry	Journal of Organic Chemistry, 2, 2.53% Journal of Organic Chemistry 2 publications, 2.53%
ACS Macro Letters	ACS Macro Letters, 2, 2.53% ACS Macro Letters 2 publications, 2.53%
Physical Chemistry Chemical Physics	Physical Chemistry Chemical Physics, 2, 2.53% Physical Chemistry Chemical Physics 2 publications, 2.53%
Materials Horizons	Materials Horizons, 2, 2.53% Materials Horizons 2 publications, 2.53%
Molecules	Molecules, 1, 1.27% Molecules 1 publication, 1.27%
Journal of Photochemistry and Photobiology A: Chemistry	Journal of Photochemistry and Photobiology A: Chemistry, 1, 1.27% Journal of Photochemistry and Photobiology A: Chemistry 1 publication, 1.27%
Progress in Polymer Science	Progress in Polymer Science, 1, 1.27% Progress in Polymer Science 1 publication, 1.27%
Chemical Engineering Journal	Chemical Engineering Journal, 1, 1.27% Chemical Engineering Journal 1 publication, 1.27%
Matter	Matter, 1, 1.27% Matter 1 publication, 1.27%
Materials Today Chemistry	Materials Today Chemistry, 1, 1.27% Materials Today Chemistry 1 publication, 1.27%
Chemical Physics Letters	Chemical Physics Letters, 1, 1.27% Chemical Physics Letters 1 publication, 1.27%
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 1, 1.27% Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 1 publication, 1.27%
Journal of Physical Organic Chemistry	Journal of Physical Organic Chemistry, 1, 1.27% Journal of Physical Organic Chemistry 1 publication, 1.27%
Macromolecular Chemistry and Physics	Macromolecular Chemistry and Physics, 1, 1.27% Macromolecular Chemistry and Physics 1 publication, 1.27%
Journal of Physical Chemistry Letters	Journal of Physical Chemistry Letters, 1, 1.27% Journal of Physical Chemistry Letters 1 publication, 1.27%
Langmuir	Langmuir, 1, 1.27% Langmuir 1 publication, 1.27%
ACS applied materials & interfaces	ACS applied materials & interfaces, 1, 1.27% ACS applied materials & interfaces 1 publication, 1.27%
Journal of Chemical Education	Journal of Chemical Education, 1, 1.27% Journal of Chemical Education 1 publication, 1.27%
	1 2 3 4 5 6 7 8 9

Citations by publishers

	5 10 15 20 25
American Chemical Society (ACS)	American Chemical Society (ACS), 24, 30.38% American Chemical Society (ACS) 24 publications, 30.38%
Wiley	Wiley, 23, 29.11% Wiley 23 publications, 29.11%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 16, 20.25% Royal Society of Chemistry (RSC) 16 publications, 20.25%
Elsevier	Elsevier, 9, 11.39% Elsevier 9 publications, 11.39%
Springer Nature	Springer Nature, 2, 2.53% Springer Nature 2 publications, 2.53%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 1.27% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 1.27%
Hindawi Limited	Hindawi Limited, 1, 1.27% Hindawi Limited 1 publication, 1.27%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 1.27% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 1.27%
	5 10 15 20 25

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Menzel J. P. et al. Wavelength Dependence of Light-Induced Cycloadditions // Journal of the American Chemical Society. 2017. Vol. 139. No. 44. pp. 15812-15820.

GOST all authors (up to 50) Copy

Menzel J. P., Noble B. T., Lauer A., Coote M. L., Blinco J. P., Barner‐Kowollik C. Wavelength Dependence of Light-Induced Cycloadditions // Journal of the American Chemical Society. 2017. Vol. 139. No. 44. pp. 15812-15820.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/jacs.7b08047

UR - https://doi.org/10.1021/jacs.7b08047

TI - Wavelength Dependence of Light-Induced Cycloadditions

T2 - Journal of the American Chemical Society

AU - Lauer, Andrea

AU - Menzel, Jan P

AU - Coote, Michelle L.

AU - Blinco, James P.

AU - Barner‐Kowollik, Christopher

AU - Noble, Benjamin T.

PY - 2017

DA - 2017/10/25 00:00:00

PB - American Chemical Society (ACS)

SP - 15812-15820

IS - 44

VL - 139

SN - 0002-7863

SN - 1520-5126

ER -

BibTex |

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BibTex Copy

@article{2017_Menzel,

author = {Andrea Lauer and Jan P Menzel and Michelle L. Coote and James P. Blinco and Christopher Barner‐Kowollik and Benjamin T. Noble},

title = {Wavelength Dependence of Light-Induced Cycloadditions},

journal = {Journal of the American Chemical Society},

year = {2017},

volume = {139},

publisher = {American Chemical Society (ACS)},

month = {oct},

url = {https://doi.org/10.1021/jacs.7b08047},

number = {44},

pages = {15812--15820},

doi = {10.1021/jacs.7b08047}

}

MLA

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Menzel, Jan P., et al. “Wavelength Dependence of Light-Induced Cycloadditions.” Journal of the American Chemical Society, vol. 139, no. 44, Oct. 2017, pp. 15812-15820. https://doi.org/10.1021/jacs.7b08047.

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Publisher

American Chemical Society (ACS)

Journal

Journal of the American Chemical Society

Quartile SCImago

Quartile WOS

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ISSN

00027863 (Print)
15205126 (Electronic)