ChemPhotoChem, volume 1, issue 5, pages 159-163

Understanding Reactivity Patterns in Light-Induced Nitrile Imine Mediated Tetrazole-Ene Cycloadditions

Eva Blasco ^{1, 2}

Yuuki Sugawara ^{1, 2}

Paul Lederhose ^{1, 3}

James P. Blinco ³

Anne-Marie Kelterer ⁴

Christopher Barner‐Kowollik ^{1, 2, 3}

Hide authors affiliations Show authors affiliations: 4 affiliations

Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie; Karlsruhe Institute of Technology (KIT); Engesserstrasse 18 76128 Karlsruhe Germany |

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

School of Chemistry, Physics and Mechanical Engineering; Queensland University of Technology (QUT); 2 George Street Brisbane, QLD 4001 Australia |

⁴

Institute of Physical and Theoretical Chemistry, NAWI Graz; Graz University of Technology; Stremayrgasse 9 8010 Graz Austria |

Publication type: Journal Article

Publication date: 2017-01-25

Wiley

Journal: ChemPhotoChem

Quartile SCImago

Quartile WOS

Impact factor: 3.7

ISSN: 23670932, 23670932

DOI: 10.1002/cptc.201600042

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Organic Chemistry

Physical and Theoretical Chemistry

Analytical Chemistry

Abstract

A rationale for predicting photochemical tetrazole activation in the popular nitrile imine mediated tetrazole–ene cycloaddition (NITEC) reaction, based on a combined theoretical and experimental study, is reported. DFT calculations of three tetrazole derivatives reveal that the efficiency of intersystem crossing is determined by the chromophore moiety. This species is critical in dictating the reactivity of the tetrazoles towards nitrile imine formation, yet mere inspection of the chromophore moiety's absorptivity is insufficient for predicting the tetrazole's photochemical reactivity.

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Chemistry - A European Journal	Chemistry - A European Journal, 3, 10.34% Chemistry - A European Journal 3 publications, 10.34%
Chemical Communications	Chemical Communications, 3, 10.34% Chemical Communications 3 publications, 10.34%
Journal of the American Chemical Society	Journal of the American Chemical Society, 2, 6.9% Journal of the American Chemical Society 2 publications, 6.9%
Journal of Organic Chemistry	Journal of Organic Chemistry, 2, 6.9% Journal of Organic Chemistry 2 publications, 6.9%
Biomolecules	Biomolecules, 1, 3.45% Biomolecules 1 publication, 3.45%
Photochemical and Photobiological Sciences	Photochemical and Photobiological Sciences, 1, 3.45% Photochemical and Photobiological Sciences 1 publication, 3.45%
ChemPhysChem	ChemPhysChem, 1, 3.45% ChemPhysChem 1 publication, 3.45%
Progress in Polymer Science	Progress in Polymer Science, 1, 3.45% Progress in Polymer Science 1 publication, 3.45%
Journal of Physical Chemistry A	Journal of Physical Chemistry A, 1, 3.45% Journal of Physical Chemistry A 1 publication, 3.45%
ACS Sensors	ACS Sensors, 1, 3.45% ACS Sensors 1 publication, 3.45%
Chemical Reviews	Chemical Reviews, 1, 3.45% Chemical Reviews 1 publication, 3.45%
Macromolecules	Macromolecules, 1, 3.45% Macromolecules 1 publication, 3.45%
ACS Macro Letters	ACS Macro Letters, 1, 3.45% ACS Macro Letters 1 publication, 3.45%
Analytical Chemistry	Analytical Chemistry, 1, 3.45% Analytical Chemistry 1 publication, 3.45%
JACS Au	JACS Au, 1, 3.45% JACS Au 1 publication, 3.45%
Chemical Science	Chemical Science, 1, 3.45% Chemical Science 1 publication, 3.45%
Materials Horizons	Materials Horizons, 1, 3.45% Materials Horizons 1 publication, 3.45%
Polymer Chemistry	Polymer Chemistry, 1, 3.45% Polymer Chemistry 1 publication, 3.45%
RSC Advances	RSC Advances, 1, 3.45% RSC Advances 1 publication, 3.45%
Advanced Functional Materials	Advanced Functional Materials, 1, 3.45% Advanced Functional Materials 1 publication, 3.45%
RSC Chemical Biology	RSC Chemical Biology, 1, 3.45% RSC Chemical Biology 1 publication, 3.45%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 3.45% Russian Chemical Reviews 1 publication, 3.45%
	1 2 3

Citations by publishers

	2 4 6 8 10 12
American Chemical Society (ACS)	American Chemical Society (ACS), 11, 37.93% American Chemical Society (ACS) 11 publications, 37.93%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 8, 27.59% Royal Society of Chemistry (RSC) 8 publications, 27.59%
Wiley	Wiley, 5, 17.24% Wiley 5 publications, 17.24%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 3.45% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 3.45%
Springer Nature	Springer Nature, 1, 3.45% Springer Nature 1 publication, 3.45%
Elsevier	Elsevier, 1, 3.45% Elsevier 1 publication, 3.45%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 3.45% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 3.45%
	2 4 6 8 10 12

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Blasco E. et al. Understanding Reactivity Patterns in Light-Induced Nitrile Imine Mediated Tetrazole-Ene Cycloadditions // ChemPhotoChem. 2017. Vol. 1. No. 5. pp. 159-163.

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Blasco E., Sugawara Y., Lederhose P., Blinco J. P., Kelterer A., Barner‐Kowollik C. Understanding Reactivity Patterns in Light-Induced Nitrile Imine Mediated Tetrazole-Ene Cycloadditions // ChemPhotoChem. 2017. Vol. 1. No. 5. pp. 159-163.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1002/cptc.201600042

UR - https://doi.org/10.1002/cptc.201600042

TI - Understanding Reactivity Patterns in Light-Induced Nitrile Imine Mediated Tetrazole-Ene Cycloadditions

T2 - ChemPhotoChem

AU - Lederhose, Paul

AU - Blasco, Eva

AU - Sugawara, Yuuki

AU - Blinco, James P.

AU - Kelterer, Anne-Marie

AU - Barner‐Kowollik, Christopher

PY - 2017

DA - 2017/01/25 00:00:00

PB - Wiley

SP - 159-163

IS - 5

VL - 1

SN - 2367-0932

ER -

BibTex |

Cite this

BibTex Copy

@article{2017_Blasco,

author = {Paul Lederhose and Eva Blasco and Yuuki Sugawara and James P. Blinco and Anne-Marie Kelterer and Christopher Barner‐Kowollik},

title = {Understanding Reactivity Patterns in Light-Induced Nitrile Imine Mediated Tetrazole-Ene Cycloadditions},

journal = {ChemPhotoChem},

year = {2017},

volume = {1},

publisher = {Wiley},

month = {jan},

url = {https://doi.org/10.1002/cptc.201600042},

number = {5},

pages = {159--163},

doi = {10.1002/cptc.201600042}

}

MLA

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MLA Copy

Blasco, Eva, et al. “Understanding Reactivity Patterns in Light-Induced Nitrile Imine Mediated Tetrazole-Ene Cycloadditions.” ChemPhotoChem, vol. 1, no. 5, Jan. 2017, pp. 159-163. https://doi.org/10.1002/cptc.201600042.

Found error?

Publisher

Wiley

Journal

ChemPhotoChem

Quartile SCImago

Quartile WOS

Impact factor

3.7

ISSN

23670932 (Print)
23670932 (Electronic)