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Frederik C Krebs

Publications and source records attributed to Frederik C Krebs.

9 recordsLinked to original sources
PubMed2006

Synthesis of an all-in-one molecule (for organic solar cells).

A multidomain compound with applications in the area of organic solar cells has been prepared. This all-in-one molecule compound integrates all the functionalities needed for solar cell action from light harvesting, carrier generation, and separation, to transport and contact to external electrodes. A convergent synthetic strategy with some 60 steps involving preparation of regioregular oligothiophenes, a zinc porphyrin, a bisterpyridine ruthenium(II) complex, a hetero oligo phenylenevinylene and functional end groups is described. Preliminary investigations of photovoltaic devices based on the target molecule gave values of 0.18 V, 0.0044 mA cm(-2), 29% and 0.000081% for the open circuit voltage (Voc), short circuit current (Isc), fill factor (FF), and efficiency (eta). These poor values are compared to those obtained with an oligo-3-hexylthiophene which gave values of 0.7 V, 0.046 mA cm(-2), 24.6%, and 0.0081% for the open circuit voltage (Voc), short circuit current (Isc), fill factor (FF) and efficiency (eta). This latter compound was also studied in a bulk heterojunction device with PCBM (1:1 blend) which gave values of 0.43 V, 0.45 mA cm(-2), 33.5%, and 0.063%.

Journal Article↗
PubMed2005

Stepwise unidirectional synthesis of oligo phenylene vinylenes with a series of monomers. Use in plastic solar cells.

Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}benzyl)phosphonic acid diethyl ester, (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]vinyl}thiophene-2-ylmethyl)phosphonic acid diethyl ester, (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}thiophene-2-ylmethyl)phosphonic acid diethyl ester, and (7-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]vinyl}benzo[1,2,5]thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C(60) derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.

Journal Article↗
PubMed2004

Stepwise and directional synthesis of end-functionalized single-oligomer OPVs and their application in organic solar cells.

A new stepwise directional synthetic route to single-oligomer p-phenylenevinylenes (OPVs) has been developed. The first step in the reaction sequence is the condensation of a functionalized benzaldehyde with a novel monomer having a methyl phosphonate ester group in one end and an acetal-protected aldehyde at the other end of a stilbene core. Oligomerization then proceeds stepwise by alternating reaction of the previous aldehyde-terminated OPV fragment with the monomer and deprotection of the acetal. Thus, a series of OPVs with 3, 5, 7, 9, and 11 phenylene vinylene units has been prepared that has an electron-donating methoxy group at one end and an electron-accepting aldehyde group at the other end. Some examples where a dimethylamino group replaced the methoxy group were also prepared. The oligomer with seven phenylene vinylene units was then further derivatized at the aldehyde position to create a series of OPVs with a range of substituents from strongly electron-accepting nitrophenyl to electron-donating methoxyphenyl. Photovoltaic cells were assembled with the synthesized OPVs as the photoactive layer. Illumination under simulated sunlight (AM1.5) gave short circuit currents (Isc) in the range 0.015-0.5 mA cm(-2) and typical open circuit voltages (Voc) of 0.4-0.8 V. The maximum efficiency obtained was approximately 0.1%.

Journal Article↗
PubMed2004

Ferromagnetic ordering in bis(benzene)chromium(+) Bis(4,5-dimethoxybenzene-1,2-dithiolato)nickel(-).

The compound bis(benzene)chromium(+) bis(4,5-dimethoxy-1,2-benzenedithiolato)nickel(-), [Cr(bz)(2)](+)[Ni(dmox)(2)](-), was prepared as well-defined crystals by a metathesis reaction. X-ray single-crystal structure confirms the expected symmetries of the cations (D6h) and anions (D2h). The Ni-S bond length is typical for a monoanionic bis(arene)-1,2-dithiolato nickel complex thus confirming the ascribed charges. The structure reveals interpenetrating cation and anion sublattices where all ions are well separated from other ions of the same charge and with almost perpendicular symmetry planes of cations and anions. Above ca. 10 K the compound is paramagnetic and follows the Curie-Weiss law for S = 1/2 on each ion with a Weiss temperature of 8.5 K. Magnetic susceptibility and magnetization studies reveal the transition to a ferromagnetically ordered phase at 3.4 K. The ferromagnetic interaction is likely to occur through short contacts between anion heteroatoms (O and Ni) and cation H atoms, forming a 2-D network. A third dimension is possible through somewhat longer interionic S-H contacts. The Curie-Weiss law behavior can be modeled for 1-D chains with a ferromagnetic interaction of J = 11.6 K.

Journal Article↗
PubMed2003

Directional synthesis of a dye-linked conducting homopolymer.

We report a new synthesis of a 10,20-diphenyl-5,15-bis(4-cyanophenyl)porphyrin (1) and its reduction to give 10,20-diphenyl-5,15-bis(4-formylphenyl)porphyrin (2). When the conducting polymer poly(2',5'-dioctyl-4,4' '-terphenylenecyanovinylene) was prepared in the presence of 2, we obtained a three-domain structure, compound 3, consisting of two homopolymer blocks (J domains) with the porphyrin dye molecule (P domain) in the middle. The JPJ assembly was subjected to photophysical studies where we showed that the J domain could serve as a light-harvesting antenna for the P domain.

Journal Article↗
PubMed2002

An exceptional red shift of emission maxima upon fluorine substitution.

The effect of perfluorination on photophysical properties was investigated through synthesis and photophysical characterization of two isostructural donor-acceptor-donor dye molecules. The synthesis of two versatile fluorinated benzene compounds, 1,4-difluoro-2,5-diperfluorooctylbenzene (1) and 1,4-dibromo-2,5-difluoro-3,6-diperfluorooctylbenzene (2), is presented. The X-ray structure of 2 has been determined and shows that the perfluorinated octyl chains segregate from the benzene rings in the solid state, giving rise to a layered structure. The further synthesis through Suzuki coupling reactions using 4-formylbenzeneboronic acid with (2) and 1,4-dibromo-2,5-dioctylbenzene (3) gave, respectively, 1,4' '-diformyl-2',5'-difluoro-3',6'-diperfluorooctyl-p-terphenylene (4) and 1,4' '-diformyl-2',5'-dioctyl-p-terphenylene (5). The condensation of the dialdehydes 4 and 5 with 9,10-phenanthrenequinone and ammoniumbicarbonate in glacial acetic acid gave the dye molecules 1,4' '-bis(1H-phenanthro[9,10-d]imidazol-2-yl)-2',5'-difluoro-3',6'-diperfluorooctyl-p-terphenylene (6) and 1,4' '-bis(1H-phenanthro[9,10-d]imidazol-2-yl)-2',5'-dioctyl-p-terphenylene (7), respectively. The UV-vis spectra of the two molecules are nearly identical, whereas the fluorescence spectra are very different. Compound 7 shows blue fluorescence with little solvent dependence (lambda(emission) = 410 nm in THF, CH2Cl2, and hexane), whereas compound 6 shows a highly solvent-dependent emission wavelength (lambda(emission) = 583 nm in THF, lambda(emission) = 560 nm in CH2Cl2, and lambda(emission) = 450 nm in hexane). The fluorescence red shift of compound 6 in a series of solvents with different polarity is discussed using the Lippert-Mataga equation. Fluorescence lifetime and quantum yields were also determined. Ultraviolet photoelectron spectroscopy (UPS) was performed on thin films of compound 6 and 7 on a gold substrate. The observed ionization potential was 6.15 eV for 6 and 5.85 eV for 7" [correction].

Journal Article↗
PubMed2002

Synthesis and structural characterization of new stiff rod oligomeric domains by X-ray crystallography and NMR.

The monomers N,N'-dibenzylbenzene-1,4-diamine (1), N,N'-dibenzylnaphthalene-1,5-diamine (2), and N,N'-dibenzylanthracene-1,9-diamine (3) were reacted with phosgene in the presence of a base to produce the corresponding N,N'-dibenzyl-1,4-bis(chlorocarbonylamino)benzene (4), N,N'-dibenzyl-1,5-bis(chlorocarbonylamino)naphthalene (5), and N,N'-dibenzyl-9,10-bis(chlorocarbonylamino)anthracene (6). These monomers were used to create zigzag type stacks, in a stepwise fashion, of trimers and 9-mers of either 1,4-diureidobenzenes ((Phe)K(3) and (Phe)K(9)) or 1,5-diureidonaphthalenes ((Nap)K(3) and (Nap)K(9)). A byproduct in the formation of (Phe)K(9) was a cyclic hexamer (Phe)K(6). NMR gave evidence of the structure in solution while X-ray crystallographic information was obtained for 5, 6, (Nap)K(3), and the cyclic (Phe)K(6).

Crystallography, X-Ray↗