Optimized synthesis and detailed NMR spectroscopic characterization of the 1,8a-dihydroazulene-1,1-dicarbonitrile photoswitch

Søren Lindbæk Broman; Sophie Lehn Brand; Christian Richard Parker; Michael Åxman Petersen; Christian Tortzen; Anders Kadziola; Kristine Kilså; Mogens Brøndsted Nielsen

Optimized synthesis and detailed NMR spectroscopic characterization of the 1,8a-dihydroazulene-1,1-dicarbonitrile photoswitch

Søren Lindbæk Broman, Sophie Lehn Brand, Christian Richard Parker, Michael Åxman Petersen, Christian Tortzen, Anders Kadziola, Kristine Kilså, Mogens Brøndsted Nielsen

Department of Chemistry

50 Citations (Scopus)

Abstract

An economical and effective protocol for large scale synthesis of the 2-phenyl-1,8adihydroazulene-1,1-dicarbonitrile (DHA) photoswitch has been developed. This compound is ring-opened by light to a vinylheptafulvene (VHF), which is thermally closed back to DHA. This compound serves as an important starting material for dihydroazulene photoswitches incorporating a substituent in the seven-membered ring and as a reference compound for comparison of properties. A detailed NMR spectroscopic characterization has allowed the assignment of all proton and carbon signals. In addition, the compound was characterized by Xray crystallography. A correlation between the rate constant for thermal ring-closure of VHF to DHA and empirical parameters of solvent polarity (E_T (30)) was established.

Original language	English
Journal	Arkivoc
Volume	ix
Pages (from-to)	51-67
ISSN	1424-6376
Publication status	Published - 19 Apr 2011

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title = "Optimized synthesis and detailed NMR spectroscopic characterization of the 1,8a-dihydroazulene-1,1-dicarbonitrile photoswitch",

abstract = "An economical and effective protocol for large scale synthesis of the 2-phenyl-1,8adihydroazulene-1,1-dicarbonitrile (DHA) photoswitch has been developed. This compound is ring-opened by light to a vinylheptafulvene (VHF), which is thermally closed back to DHA. This compound serves as an important starting material for dihydroazulene photoswitches incorporating a substituent in the seven-membered ring and as a reference compound for comparison of properties. A detailed NMR spectroscopic characterization has allowed the assignment of all proton and carbon signals. In addition, the compound was characterized by Xray crystallography. A correlation between the rate constant for thermal ring-closure of VHF to DHA and empirical parameters of solvent polarity (ET (30)) was established.",

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T1 - Optimized synthesis and detailed NMR spectroscopic characterization of the 1,8a-dihydroazulene-1,1-dicarbonitrile photoswitch

AU - Broman, Søren Lindbæk

AU - Brand, Sophie Lehn

AU - Parker, Christian Richard

AU - Petersen, Michael Åxman

AU - Tortzen, Christian

AU - Kadziola, Anders

AU - Kilså, Kristine

AU - Nielsen, Mogens Brøndsted

PY - 2011/4/19

Y1 - 2011/4/19

N2 - An economical and effective protocol for large scale synthesis of the 2-phenyl-1,8adihydroazulene-1,1-dicarbonitrile (DHA) photoswitch has been developed. This compound is ring-opened by light to a vinylheptafulvene (VHF), which is thermally closed back to DHA. This compound serves as an important starting material for dihydroazulene photoswitches incorporating a substituent in the seven-membered ring and as a reference compound for comparison of properties. A detailed NMR spectroscopic characterization has allowed the assignment of all proton and carbon signals. In addition, the compound was characterized by Xray crystallography. A correlation between the rate constant for thermal ring-closure of VHF to DHA and empirical parameters of solvent polarity (ET (30)) was established.

AB - An economical and effective protocol for large scale synthesis of the 2-phenyl-1,8adihydroazulene-1,1-dicarbonitrile (DHA) photoswitch has been developed. This compound is ring-opened by light to a vinylheptafulvene (VHF), which is thermally closed back to DHA. This compound serves as an important starting material for dihydroazulene photoswitches incorporating a substituent in the seven-membered ring and as a reference compound for comparison of properties. A detailed NMR spectroscopic characterization has allowed the assignment of all proton and carbon signals. In addition, the compound was characterized by Xray crystallography. A correlation between the rate constant for thermal ring-closure of VHF to DHA and empirical parameters of solvent polarity (ET (30)) was established.

M3 - Journal article

SN - 1551-7004

VL - ix

SP - 51

EP - 67

JO - A R K I V O C

JF - A R K I V O C

ER -

Optimized synthesis and detailed NMR spectroscopic characterization of the 1,8a-dihydroazulene-1,1-dicarbonitrile photoswitch

Abstract

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