Syntheses, structures, two-photon absorption cross-sections and computed second hyperpolarisabilities of quadrupolar A-π-A systems containing E-dimesitylborylethenyl acceptors - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Journal of Materials Chemistry Année : 2009

Syntheses, structures, two-photon absorption cross-sections and computed second hyperpolarisabilities of quadrupolar A-π-A systems containing E-dimesitylborylethenyl acceptors

Résumé

A series of bis(E-dimesitylborylethenyl)-substituted arenes, namely arene = 1,4-benzene, 1,4-tetrafluorobenzene, 2,5-thiophene, 1,4-naphthalene, 9,10-anthracene, 4,4′-biphenyl, 2,7-fluorene, 4,4′-E-stilbene, 4,4′-tolan, 5,5′-(2,2′-bithiophene), 1,4-bis(4-phenylethynyl)benzene, 1,4-bis(4-phenylethynyl)tetrafluorobenzene and 5,5″-(2,2′:5′,2″-terthiophene), have been synthesised via hydroboration of the corresponding diethynylarenes with dimesitylborane. Their absorption and emission maxima, fluorescence lifetimes and quantum yields are reported along with the two-photon absorption (TPA) spectra and TPA cross-sections for the 5,5′-bis(E-dimesitylborylethenyl)-2,2′-bithiophene and 5,5′-bis(E-dimesitylborylethenyl)-2,2′:5′,2″-terthiophene derivatives. The TPA cross-section of the latter compound of ca. 1800 GM is the largest yet reported for a 3-coordinate boron compound and is in the range of the largest values measured for quadrupolar compounds with similar conjugation lengths. The X-ray crystal structures of 1,4-benzene, 2,5-thiophene, 4,4′-biphenyl and 5,5″-(2,2′:5′,2″-terthiophene) derivatives indicate π-conjugation along the BC[double bond, length as m-dash]C-arene-C[double bond, length as m-dash]CB chain. Theoretical studies show that the second molecular hyperpolarisabilities, γ, in each series of compounds are generally related to the HOMO energy, which itself increases with increasing donor strength of the spacer. A strong enhancement of γ is predicted as the number of thiophene rings in the spacer increases.
Fichier principal
Vignette du fichier
b905719f.pdf (762.91 Ko) Télécharger le fichier
Origine : Fichiers éditeurs autorisés sur une archive ouverte

Dates et versions

hal-00861600 , version 1 (13-09-2013)

Identifiants

Citer

Christopher D. Entwistle, Jonathan C. Collings, Andreas Steffen, Lars-Olof Palsson, Andrew Beeby, et al.. Syntheses, structures, two-photon absorption cross-sections and computed second hyperpolarisabilities of quadrupolar A-π-A systems containing E-dimesitylborylethenyl acceptors. Journal of Materials Chemistry, 2009, 19, pp.7532-7544. ⟨10.1039/B905719F⟩. ⟨hal-00861600⟩
178 Consultations
259 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More