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

Kemisk Institut

50 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Arkivoc
Vol/bind	ix
Sider (fra-til)	51-67
ISSN	1424-6376
Status	Udgivet - 19 apr. 2011

Citationsformater

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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.",

author = "Broman, {S{\o}ren Lindb{\ae}k} and Brand, {Sophie Lehn} and Parker, {Christian Richard} and Petersen, {Michael {\AA}xman} and Christian Tortzen and Anders Kadziola and Kristine Kils{\aa} and Nielsen, {Mogens Br{\o}ndsted}",

year = "2011",

month = apr,

day = "19",

language = "English",

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pages = "51--67",

journal = "A R K I V O C",

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TY - JOUR

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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