Structure and Raman spectra of pyridyl substituted diketo-pyrrolo-pyrrole isomers and polymorphs

Luňák, Stanislav; Vyňuchal, Jan; Horáčková, Pavlína; Frumarová, Božena; Žák, Zdirad; Kučerík, Jiří; Salyk, Ota

doi:10.1016/j.molstruc.2010.08.026

Cited by 17 publications

(7 citation statements)

References 14 publications

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“…Notably, electron‐poor aromatic nitriles proved to be more reactive in the DPP synthesis, as compared to electron‐rich analogues . However, to the best of our knowledge only ten papers have described diketopyrrolopyrroles possessing pyridyl substituents at positions 3 and 6 . Moreover, most of these publications focused on unsubstituted pyridine.…”

Section: Introductionsupporting

confidence: 63%

The Impact of the Interplay between Steric and Electronic Effects on the Synthesis and Optical Properties of Diketopyrrolopyrroles Bearing Pyridine Moieties

et al. 2017

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The influence of a combination of steric and electronic factors on both the preparation and the optical properties of diketopyrrolopyrroles was investigated. The attachment of a cyano group to the electron‐deficient pyridine ring overcame the negative influence of the flanking methyl group on the efficiency of the synthesis of diketopyrrolopyrroles. Diketopyrrolopyrroles possessing pyridine‐N‐oxide moieties were studied for the first time. We have also shown that reactions of cyanopyridines possessing an additional dialkylamino group were very capricious and depending on the relative position of all substituents, can lead to low yields of diketopyrrolopyrroles. The interplay between the dihedral angle between the diketopyrrolopyrrole core and the pyridyl substituents as well as the presence and position of electron‐donating moieties made it possible to modulate the photophysical properties of N,N′‐dialkyldiketopyrrolopyrroles. In particular, it was found that pyridine‐N‐oxides as the aryl moieties had a strong influence on the optical properties of diketopyrrolopyrroles, shifting both absorption and emission bands bathochromically. Two‐photon absorption cross‐sections had low values except for those dyes possessing a clear quadrupolar centrosymmetric nature.

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Section: Introductionsupporting

confidence: 63%

The Impact of the Interplay between Steric and Electronic Effects on the Synthesis and Optical Properties of Diketopyrrolopyrroles Bearing Pyridine Moieties

et al. 2017

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“…The future challenge for thermal analyses (mainly of the T g -PPV material) is the difficulty of directly assessing the materials in actual thin layers deposited on substrates and, moreover, of performing detailed DSC analyses of these materials in pure forms as well as in layers. The Brought to you by | New York University Bobst Library Technical Services Authenticated Download Date | 6/10/15 7:36 AM approach designed by Zhao et al [32] using experimental principles already proven successful for low-molecular electrically active pigments [34,35], or the use of Raman and X-ray spectrometries [36] in combination with deeper structural investigations [37], could be useful in this area. Results could be correlated and final schemes devised.…”

Section: Discussionmentioning

confidence: 99%

The influence of transport layers on the photodegradation stability of polymer solar cell structures

Možíšková

Heinrichová

Šedina

et al. 2014

Journal of Polymer Engineering

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A light exposure degradation study of electrically active polymers -high-glass-transition-temperature poly(1,4-phenylenevinylene) (T g -PPV); poly(3-hexylthiophene-2,5-diyl) (P3HT); and poly(2-methoxy-5-(3′-7′-dimethyloctyloxy)-1,4-phenylenevinylene) (MDMO-PPV) -in pure form and blends with [6,6]-phenyl C 61 -butyric acid methyl ester (PCBM) was conducted to assess the influence of the employed transport layers on the materials' photodegradation stability. Devices were prepared on quartz glass and silicon (Si) substrates with a transport layer prepared from poly(3,4-ethylenedioxythiophene):poly(4-styrene sulfonate) (PEDOT:PSS) or titanium dioxide (TiO 2 ). Photodegradation processes in ambient air demonstrated that the polymers were thermally stable in the dark; thus, the material deteriorations not only were caused by thermal stress, but also from light-induced processes. Degradation processes of pure polymers may be considered as fast -in the order of hours -but retardable by blending of polymers with PCBM. The deposition of polymer blends on an additional layer of PEDOT:PSS or TiO 2 revealed that the polymer blends studied in this work (except for P3HT) presented higher stability against polymer chain scission when deposited onto the TiO 2 layer. Kinetic analysis undertaken during this work revealed that the photodegradation processes were followed by two degradation steps. Degradation kinetics were evaluated according to a Perrin-like model for absorption assessments and according to simple exponential for emission measurements.

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“…1 Therefore, they found applications in molecular imaging, 2 DNA detection, 3 anion/cation recognition, 4 sensing, 5 field effect transistors (FET), 6 aggregation-induced emission (AIE), 7 circularly polarized luminescence (CPL), 8 or solar cells. [9][10][11] They are usually prepared by reaction of an aromatic nitrile with dialkyl succinate, which allows to attach a large variety of aromatic groups on the DPP core, such as phenyl, 12 pyridine, 13 thiophene 14,15 or selenophene. 16 Although Cu(I), Ag(I) and Au(I) complexes of bis(deprotonated) dianionic DPP derivatives have been reported already in 2000 by Lorenz et al, 17,18 the coordination and organometallic chemistry of DPP based ligands started to be more systematically explored in the last decade, 19 yet their number remains very limited to date.…”

Section: Introductionmentioning

confidence: 99%

“…The extra peak at 1.56 ppm comes from H2O solvent molecules 13. C-NMR of the sample was not successful because of its low solubility in the chosen solvent (please see attached figure in the SI).…”

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Thiophene–Bipyridine Appended Diketopyrrolopyrrole Ligands and Platinum(II) Complexes

et al. 2021

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Straightforward palladium (II) catalyzed direct cross-coupling reaction between decyl, (S)-2-methylbutyl and dodecyl N-substituted diketopyrrolopyrrole thiophene (DPPT), including a 3-methoxythiophene derivative, and 6-bromo-2,2'-bipyridine afforded a series of mono-and bis-bipyridine substituted DPPT ligands 1-3. Complexation reactions with PtCl2(DMSO)2 provided ortho-metalated platinum (II) complexes 1-Pt and 2-Pt, together with the N^N^O complex 3d-Pt(N^N^O) resulted from the O-Me activation of the intermediary complex 3d-Pt(N^N). The ligand 1b and the mononuclear complexes 1a-Pt and 1b-Pt have been structurally characterized by single crystal X-ray structure, evidencing the establishment of numerous intermolecular p-p interactions in the solid state. Moreover, in the crystal structure of the model complex DMTB-Pt(N^N^O) (DMTB = 3,4-dimethoxy-(2,2'-bipyridine)) the chelating tridentate N^N^O mode is clearly evidenced. The chiral ligand 1b and its mononuclear complex 1b-Pt do not show any CD signal in solution, but they are CD active in the solid state, with bisignate bands in the low energy region, opposite in sign between the ligand and the complex, suggesting helical supramolecular arrangement of the dpp chromophore in the solid state. Photophysical investigations demonstrate that all the ligands are fluorescent, with high quantum yields, while the emission is quenched for the complexes, except partially in 3d-Pt(N^N), very likely through an intersystem crossing mechanism promoted by the heavy metal. DFT calculations support the differences observed between the absorption properties of the ligands, orthoand non orthometalated complexes. The highly fluorescent bipyridine ligands reported herein open the way towards multifunctional transition metal complexes and their use in organic electronics.

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Structure and Raman spectra of pyridyl substituted diketo-pyrrolo-pyrrole isomers and polymorphs

Cited by 17 publications

References 14 publications

The Impact of the Interplay between Steric and Electronic Effects on the Synthesis and Optical Properties of Diketopyrrolopyrroles Bearing Pyridine Moieties

The Impact of the Interplay between Steric and Electronic Effects on the Synthesis and Optical Properties of Diketopyrrolopyrroles Bearing Pyridine Moieties

The influence of transport layers on the photodegradation stability of polymer solar cell structures

Thiophene–Bipyridine Appended Diketopyrrolopyrrole Ligands and Platinum(II) Complexes

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