0000000000150369
AUTHOR
Dirk Ickenroth
showing 6 related works from this author
Preparation and nonlinear optics of monodisperse oligo(1,4-phenyleneethynylene)s
2001
Oligo(1,4-phenyleneethynylene)s 1a−e, with solubilizing propoxy side chains, were prepared by use of Hagihara−Sonogashira coupling reactions. The synthetic strategy was based on a building block system and on the use of trimethylsilyl and triisopropylsilyl protecting groups that could be cleaved selectively. The extension of the conjugation with an increasing number of repeat units provokes a bathochromic shift of the long wavelength absorption and a superlinear increase of the second hyperpolarizability |γ|. The corresponding third harmonic generation (THG) measurements were performed using polystyrene matrices and variable laser wavelengths. We conclude that the conjugation length is much…
ChemInform Abstract: Preparation and Nonlinear Optics of Monodisperse Oligo(1,4-phenyleneethynylene)s.
2010
Oligo(1,4-phenyleneethynylene)s 1a−e, with solubilizing propoxy side chains, were prepared by use of Hagihara−Sonogashira coupling reactions. The synthetic strategy was based on a building block system and on the use of trimethylsilyl and triisopropylsilyl protecting groups that could be cleaved selectively. The extension of the conjugation with an increasing number of repeat units provokes a bathochromic shift of the long wavelength absorption and a superlinear increase of the second hyperpolarizability |γ|. The corresponding third harmonic generation (THG) measurements were performed using polystyrene matrices and variable laser wavelengths. We conclude that the conjugation length is much…
Oligomere aus gleichsinnig angeordneten Chalkon-Bausteinen
1999
The cross-conjugated oligomers 1a–d, which contain up to eight alternately arranged chalcone building blocks, were prepared by stereoselective condensation reactions of formyl and acetyl components. The synthetic sequence started with 1,4-dibromo-2,5-dipropoxybenzene (2). Bouveault reactions with DMF and DMA yielded the aldehydes 3 and 6 and the ketones 7 and 10. After the protection of the carbonyl group (3 4 and 7 8), a further Bouveault reaction led to monoprotected dialdehyd 5 and diketone 9, respectively. Repetitive condensation reactions starting with the acetophenone derivative 11 and 5 furnished the aldehyde 12, the ketone 13 and the aldehyde 14. In the final step the target compoun…
Monodisperse Oligo(2,5-dipropoxy-1,4-phenyleneethynylene)s
2002
Oligo(phenyleneethynylene)s 1 are rod-like compounds with undisturbed conjugation. In supplementation of the previously described members of this series 1a−e, with repeating units of up to n = 5, this work contains the preparation of higher oligomers 1f−i (n = 6, 7, 8, 10) through the use of the Sonogashira−Hagihara reaction. Both the absorption and the fluorescence bands showed convergence for increasing values of n, reaching limiting values at the effective conjugation length of nECL = 10. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
Pentadecamer 2,5-Dipropoxy-1,4-phenylenevinylene
2002
The conjugated, all-(E)-configured pentadecamer 2,5-dipropoxy-1,4-phenylenevinylene 1j was prepared by a multistep synthesis on the basis of hydroquinone. The procedure consists of a general method for the repetitive extension of oligo(phenylenvinylene) chains by two styryl units (7a ⇄ 10 ⇄ 12 ⇄ 14). The relatively rigid oligomer 1j represents a molecular wire of about 100 A. The absorption of 1j provides a proof for the convergence theory for electronic properties of conjugated oligomers with increasing number of repeat units. The corresponding conjugated polymer 1p with the same substitution matches the values which were extrapolated from the oligomer series 1a−1j. (© Wiley-VCH Verlag Gmb…
Konvergenz von Absorption und Fluoreszenz bei gekreuzt konjugierten Oligomeren aus Chalkon-Bausteinen
1999
The absorption and fluorescence spectra of two series of chalcone oligomers (1a–d) and (2a–d) are reported. Due to small or vanishing orbital coefficients (HMO calculation) within the cross-conjugated systems, the bathochromic shifts caused by the extension of the chains are modest. The effective conjugation lengths amount to 6 and 14 chalcone building blocks in the absorptions of the series 1 and 2. The convergence of the fluorescence bands is already reached in 1d and 2d with 4 and 8 enone units, respectively. Besides the uniform or alternate arrangement of the chalcone building blocks, the positions of the propoxy substituents show a considerable influence on the electronic transitions p…