CuAAC and RuAAC with alkyne-functionalised Dihydroazulene photoswitches and determination of Hammett σ-constants for Triazoles

Henriette Schjøtt Lissau; Søren Lindbæk Broman; Martyn Jevric; Anders Østergaard Madsen; Mogens Brøndsted Nielsen

doi:10.1071/ch13544

CuAAC and RuAAC with alkyne-functionalised Dihydroazulene photoswitches and determination of Hammett σ-constants for Triazoles

Henriette Schjøtt Lissau, Søren Lindbæk Broman, Martyn Jevric, Anders Østergaard Madsen, Mogens Brøndsted Nielsen

Department of Chemistry

5 Citations (Scopus)

Abstract

Dihydroazulene (DHA)-vinylheptafulvene (VHF) photoswitches have attracted attention as potentially useful components in molecular electronics. The p-conjugated dihydroazulene system is a rigid structure and can be strategically functionalised to place handles for further elaboration. Here we show that alkyne-functionalised dihydroazulenes can be subjected to copper and ruthenium catalysed azide-alkyne cycloadditions (CuAAC and RuAAC) with tolylazide, furnishing 1,4- and 1,5-disubstituted triazoles. The rates of ring-closure of the corresponding vinylheptafulvenes were compared with those of reference systems, which allowed determination of Hammett substituent constants (meta and para) for N-tolyl-substituted 1,2,3-triazoles.

Original language	English
Journal	Australian Journal of Chemistry
Volume	67
Issue number	3
Pages (from-to)	531-534
Number of pages	4
ISSN	0004-9425
DOIs	https://doi.org/10.1071/ch13544
Publication status	Published - 2014

Access to Document

10.1071/ch13544

Cite this

@article{4adfc98f2bdf4f9cb41301bb07ccb90b,

title = "CuAAC and RuAAC with alkyne-functionalised Dihydroazulene photoswitches and determination of Hammett σ-constants for Triazoles",

abstract = "Dihydroazulene (DHA)-vinylheptafulvene (VHF) photoswitches have attracted attention as potentially useful components in molecular electronics. The p-conjugated dihydroazulene system is a rigid structure and can be strategically functionalised to place handles for further elaboration. Here we show that alkyne-functionalised dihydroazulenes can be subjected to copper and ruthenium catalysed azide-alkyne cycloadditions (CuAAC and RuAAC) with tolylazide, furnishing 1,4- and 1,5-disubstituted triazoles. The rates of ring-closure of the corresponding vinylheptafulvenes were compared with those of reference systems, which allowed determination of Hammett substituent constants (meta and para) for N-tolyl-substituted 1,2,3-triazoles.",

author = "Lissau, {Henriette Schj{\o}tt} and Broman, {S{\o}ren Lindb{\ae}k} and Martyn Jevric and Madsen, {Anders {\O}stergaard} and Nielsen, {Mogens Br{\o}ndsted}",

year = "2014",

doi = "10.1071/ch13544",

language = "English",

volume = "67",

pages = "531--534",

journal = "Australian Journal of Chemistry",

issn = "0004-9425",

publisher = "C S I R O Publishing",

number = "3",

}

TY - JOUR

T1 - CuAAC and RuAAC with alkyne-functionalised Dihydroazulene photoswitches and determination of Hammett σ-constants for Triazoles

AU - Lissau, Henriette Schjøtt

AU - Broman, Søren Lindbæk

AU - Jevric, Martyn

AU - Madsen, Anders Østergaard

AU - Nielsen, Mogens Brøndsted

PY - 2014

Y1 - 2014

N2 - Dihydroazulene (DHA)-vinylheptafulvene (VHF) photoswitches have attracted attention as potentially useful components in molecular electronics. The p-conjugated dihydroazulene system is a rigid structure and can be strategically functionalised to place handles for further elaboration. Here we show that alkyne-functionalised dihydroazulenes can be subjected to copper and ruthenium catalysed azide-alkyne cycloadditions (CuAAC and RuAAC) with tolylazide, furnishing 1,4- and 1,5-disubstituted triazoles. The rates of ring-closure of the corresponding vinylheptafulvenes were compared with those of reference systems, which allowed determination of Hammett substituent constants (meta and para) for N-tolyl-substituted 1,2,3-triazoles.

AB - Dihydroazulene (DHA)-vinylheptafulvene (VHF) photoswitches have attracted attention as potentially useful components in molecular electronics. The p-conjugated dihydroazulene system is a rigid structure and can be strategically functionalised to place handles for further elaboration. Here we show that alkyne-functionalised dihydroazulenes can be subjected to copper and ruthenium catalysed azide-alkyne cycloadditions (CuAAC and RuAAC) with tolylazide, furnishing 1,4- and 1,5-disubstituted triazoles. The rates of ring-closure of the corresponding vinylheptafulvenes were compared with those of reference systems, which allowed determination of Hammett substituent constants (meta and para) for N-tolyl-substituted 1,2,3-triazoles.

U2 - 10.1071/ch13544

DO - 10.1071/ch13544

M3 - Journal article

SN - 0004-9425

VL - 67

SP - 531

EP - 534

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 3

ER -

CuAAC and RuAAC with alkyne-functionalised Dihydroazulene photoswitches and determination of Hammett σ-constants for Triazoles

Abstract

Access to Document

Fingerprint

Cite this