852435-01-9

Upstream product

• 111-25-1 1-bromo-hexane 
• 638-45-9 1-Iodohexane 

Downstream Products

• 1214906-01-0 2,5-N,N'-bis(hexyl)-3,6-bis(5-bromothiophen-2-yl)-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione 

Relevant academic research and scientific papers

Solid state supramolecular structure of diketopyrrolopyrrole chromophores: Correlating stacking geometry with visible light absorption

Mono- and di-alkylated 1,4-diketo-3,6-dithiophenylpyrrolo[3-4-c]pyrrole derivatives (TDPPs) have been synthesised and their solid state packing and absorption properties have been correlated. In this library of compounds the bulkier substituents distort the geometry of the chromophores and shift the lowest energy absorption band as a consequence of reduced π-π stacking and inter-chromophore overlap. Longitudinal displacement of the conjugated core is affected by donor-acceptor intermolecular interactions and twisting of the thiophene ring out of the plane of the DPP core, whereas lateral displacement was correlated to distortion of the NLactam-C(R) bond out of the plane of the DPP core. The di-substituted TDPP with hexyl units exhibit high molecular planarity, strong close packing of the conjugated core and significant red shift of the maximum of absorption in the solid, whereas the mono-substituted compounds with hexyl and ethyl acetate units are the least distorted of the series because of strong intermolecular hydrogen bonding that increases the molecular overlap and planarity of the chromophores. Therefore the family of mono-substituted TDPPs and more specifically the ones with ethyl acetate substituents show good potential for modulating the molecular geometry and optimizing the charge transport in materials for organic electronic applications.

Intramolecular excimer formation between 3,6-di(thiophen-2-yl)pyrrolo[3,4- c]pyrrole-1,4(2H,5H)-dione chromophoric groups linked by a flexible alkyl spacer

Bichromophoric molecules containing two 3,6-di(thiophen-2-yl)pyrrolo[3,4-c] pyrrole-1,4(2H,5H)-dione (DPP) moieties linked via aliphatic spacers of different length are synthesized. Optical absorption spectroscopy indicates that the molecules adopt an extended conformation in solution. Fluorescence spectroscopy shows that photons are emitted from the locally excited singlet state in an extended conformation. In sufficiently polar solvents, quenching of fluorescence occurs and fluorescence quantum yield (ΦF) and fluorescence lifetime (τF) measurements indicate formation of an intramolecular excimer as the quenching mechanism. The redox potentials of the molecules and the solvent polarity dependence of the quenching are consistent with significant charge-transfer character of the excimer state. Photoinduced absorption measurements show enhanced intersystem crossing to the triplet state in polar solvents. Results indicate that in donor-acceptor π-conjugated materials involving the DPP moiety, excimer-like interchain polaron pair excited states could play an important role in the photophysics because of their close proximity in energy to the lowest singlet excited state.

Unprecedented rearrangement of diketopyrrolopyrroles leads to structurally unique chromophores

Diketopyrrolopyrroles possessing thienyl, furyl and benzofuryl substituents undergo unprecedented skeletal rearrangement in the presence of trimethylsilyl bromide resulting in the formation of thieno[2,3-f]isoindole-5,8-diones and furo[2,3-f]isoindole-5,8-diones. These relatively small dyes possess favorable photophysical properties with the emission maxima within the range of 573-624 nm, large fluorescence quantum yields, moderate sensitivity of emission to solvent polarity and a HOMO-LUMO gap of ca. 1.8 eV.

Towards more sustainable synthesis of diketopyrrolopyrroles

The alkylation of 1,4-diketo-3,6-arylpyrrolo[3,4-c]pyrroles (ArDPP) is one of the most important steps in the synthesis of soluble materials based on these molecules and the polymers derived from them (that are employed widely in putative organic solar ce

Diketopyrrolopyrrole compound with terminal group containing bi[n]alkynyl and application of diketopyrrolopyrrole compound

The invention relates to a diketopyrrolopyrrole compound with a terminal group containing bi[n]alkynyl and application of the diketopyrrolopyrrole compound. The diketopyrrolopyrrole compound is shown as a general molecular formula in the description, wherein R1 refers to straight-chain paraffin or branched paraffin, R2 refers to H atom, trimethylsilyl, straight-chain paraffin or branched paraffin, and n is an integer not less than 1. The diketopyrrolopyrrole compound with the terminal group containing the bi[n]alkynyl can be widely applied to organic light-emitting diodes, field-effect transistors and solar cells.

Preparation method of diketopyrrolopyrrole compound with bi[n]alkynyl-containing terminal group

The invention relates to a preparation method of a diketopyrrolopyrrole compound with a bi[n]alkynyl-containing terminal group. 3, 6-bis(thiophene-2-yl)pyrrolo[3, 4-C]pyrrole-1, 4-dione (DPP) and a bi[n]alkynyl group-containing micromolecule undergo a reaction to produce the diketopyrrolopyrrole compound and n is an integer greater than or equal to 1. The preparation method comprises that a terminal alkyne-DPP derivative and 1-alkyne undergo a Glaser coupling reaction to produce a desired product of which n is 1 or 2, or comprises that a soluble dibromo-DPP derivative and bi[n]alkyne undergo a Cadiot-Chodkiewicz coupling reaction to produce a high-yield desired product of which n is greater than or equal to 2. The diketopyrrolopyrrole compound can be widely used in fields of organic light-emitting diodes, field-effect tubes and solar cells.

Optical properties of oligothiophene substituted diketopyrrolopyrrole derivatives in the solid phase: Joint J- and H-type aggregation

Photophysical properties of diketopyrrolopyrrole derivatives substituted with oligothiophenes are investigated. All compounds are found to be fluorescent both in solution and in the solid phase. At low temperature in the solid, fluorescence originates from excimer-like excited states. Comparison of absorption and fluorescence excitation spectra taken under matrix isolated conditions and on solid films show the presence of both J- and H-type absorption bands in the solid phase. Quantum-chemical calculations, including exciton-phonon coupling to account for deviations from the Born-Oppenheimer approximation, are performed to simulate the band shape of the lowest absorption band in the molecular solid. The joint presence of J- and H-bands is explained by the presence of two molecules in the unit cell. The Davydov splitting is substantial for molecules with linear alkyl substituents on the nitrogen atom (on the order of 0.2 eV) but can be reduced to almost zero by introducing branching at the β-carbon of the alkyl side chain.

Synthesis of diketopyrrolopyrrole containing copolymers: A study of their optical and photovoltaic properties

The diketopyrrolopyrrole-based copolymers PDPP-BBT and TDPP-BBT were synthesized and used as a donor for bulk heterojunction photovoltaic devices. The photophysical properties of these polymers showed absorption in the range 500-600 nm with a maximum peak around 563 nm, while TDPP-BBT showed broadband absorption in the range 620 - 800 nm with a peak around 656 nm. The power conversion efficiencies (PCE) of the polymer solar cells based on these copolymers and [6,6]-phenyl C61 butyric acid methyl ester (PCBM) were 0.68% (as cast PDPP-BBT:PCBM), 1.51% (annealed PDPP-BBT:PCBM), 1.57% (as cast TDPPBBT:PCBM), and 2.78% (annealed TDPP-BBT:PCBM), under illumination of AM 1.5 (100 mW/cm2). The higher PCE for TDPP-BBT-based polymer solar cells has been attributed to the low band gap of this copolymer as compared to PDPP-BBT, which increases the numbers of photogenerated excitons and corresponding photocurrent of the device. These results indicate that PDPP-BBT and TDPP-BBT act as excellent electron donors for bulk heterojunction devices. ? 2010 American Chemical Society.