Acetylenic Tetrathiafulvalene Scaffolds - Intramolecular Charge-Transfer Molecules

TY - JOUR

T1 - Acetylenic Tetrathiafulvalene Scaffolds - Intramolecular Charge-Transfer Molecules

AU - Lincke, Kasper

AU - Christensen, Mikkel Andreas

AU - Diederich, Francois

AU - Nielsen, Mogens Brøndsted

PY - 2011/10

Y1 - 2011/10

N2 - Two tetrathiafulvalene-functionalized acetylenic scaffolds were synthesized by Glaser-Hay and Sonogashira coupling reactions; the one scaffold was based on a central dehydroannulene core and the other on a tetraethynylethene core. Peripheral propyl groups on the tetrathiafulvalenes ascertained solubility. The compounds are strong donor-acceptor chromophores and exhibit characteristic charge-transfer absorptions according to UV/VIS absorption spectroscopy. Furthermore, the redox properties were investigated by cyclic and differential-pulse voltammetries. The experiments allow for a direct comparison between the acceptor strengths of the two acetylenic cores, and the conclusions are supported by electron-affinity calculations.

AB - Two tetrathiafulvalene-functionalized acetylenic scaffolds were synthesized by Glaser-Hay and Sonogashira coupling reactions; the one scaffold was based on a central dehydroannulene core and the other on a tetraethynylethene core. Peripheral propyl groups on the tetrathiafulvalenes ascertained solubility. The compounds are strong donor-acceptor chromophores and exhibit characteristic charge-transfer absorptions according to UV/VIS absorption spectroscopy. Furthermore, the redox properties were investigated by cyclic and differential-pulse voltammetries. The experiments allow for a direct comparison between the acceptor strengths of the two acetylenic cores, and the conclusions are supported by electron-affinity calculations.

M3 - Journal article

SN - 0018-019X

VL - 94

SP - 1743

EP - 1753

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

ER -