Electronic and structural properties of polymers based on phenylene vinylene and thiophene units. Control of the gap by gradual increases of thiophene moieties

Sánchez, C. O.; Sobarzo, Patricio A.; Gatica, Nicolás

doi:10.1039/c5nj01671a

Cited by 17 publications

(19 citation statements)

References 37 publications

(61 reference statements)

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“…Retention of the selectivity was also confirmed by the presence of two doublets in the 1 H NMR spectrum with a coupling constant around 16 Hz for TRI‐2 tph, which has a star‐like shape with six thiophene units; nonetheless, the very low solubility of TRI‐3 tph did not allow the full assignment of this derivative. No completed assignment of similar systems was reported in other studies . MALDI‐TOF analysis confirmed unequivocally the presence of the final derivatives in all cases (Figure S1–S5).…”

Section: Resultssupporting

confidence: 50%

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Design of Assembled Systems Based on Conjugated Polyphenylene Derivatives and Carbon Nanohorns

Iglesias

Guerra

Gómez

et al. 2016

Chemistry A European J

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Promising materials have been designed and fully characterised by an effective interaction between versatile platforms such as carbon nanohorns (CNHs) and conjugated molecules based on thiophene derivatives. Easy and non-aggressive methods have been described for the synthesis and purification of the final systems. Oligothiophenephenylvinylene (OTP) systems with different geometries and electron density are coupled to the CNHs. A wide range of characterization techniques have been used to confirm the effective interaction between the donor (OTP) and the acceptor (CNH) systems. These hybrid materials show potential for integration into solar cell devices. Importantly, surface-enhanced Raman spectroscopy (SERS) effects are observed without the presence of any metal surface in the system. Theoretical calculations have been performed to study the optimised geometries of the noncovalent interaction between the surface and the organic molecule. The calculations allow information on the monoelectronic energies of HOMO-LUMO orbitals and band gap of different donor systems to be extracted.

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Section: Resultssupporting

confidence: 50%

“…To our knowledge, no detailed analyses of the 1 H and 13 C NMR data for compounds with three thiophene units is available, probably due to the overlapped peaks and the low solubility of these molecules. Here, we assigned proton and carbon signals through a set of 1D and 2D experiments.…”

Section: Resultsmentioning

confidence: 99%

Design of Assembled Systems Based on Conjugated Polyphenylene Derivatives and Carbon Nanohorns

Iglesias

Guerra

Gómez

et al. 2016

Chemistry A European J

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“…In Table are summarized the optical and electrochemical properties of the PAzMCs. The optical bandgaps ( E g opt ) were calculated from the Tauc approximation ( E g opt = 1240/ λ edge , where λ edge corresponds to the absorption edge wavelength of the lower electronic transition band) . For DMSO or THF PAzMCs solutions, the estimated bandgaps were ca 3.12 eV.…”

Section: Resultsmentioning

confidence: 99%

New cardo silylated poly(azomethine)s containing 9,9′‐diphenylfluorene units as materials with Brønsted acid‐dependent fluorescence

Hauyon

Garrido‐Gatica

Sobarzo

et al. 2019

Polymer International

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Aromatic poly(azomethine)s have been studied due to their attractive properties such as high thermal stability, semiconducting behavior and the ability to coordinate species with their imine units (CN). In this paper, the synthesis and characterization of two novel silylated poly(azomethine)s containing cardo units are reported. These materials were highly soluble in organic solvents such as chloroform and m‐cresol and were thermally stable, and PAzMC1 exhibited a high glass transition temperature value (287 °C), while that for PAzMC2 was not observed. UV–visible spectrophotometry revealed absorption bands related to the aromatic backbone of both PAzMCs, 300–285 nm in tetrahydrofuran and 310–301 nm in dimethylsulfoxide, and bands attributed to the conjugated imine unit at around 350 nm. In order to investigate the phenomenon of the emission of fluorescence promoted by dopant agents with regard to potential optoelectronic applications, the materials were doped with H2SO4 and their optical and electrochemical properties investigated. Thus, the absorption band of the imine group was suppressed due to the nitrogen atoms being protonated. Fluorescence spectroscopy analysis developed in dilute solutions of polymers showed no emission from the undoped polymers, whereas the acid‐doped species emitted fluorescence in the UV and violet regions (322 nm). Cyclic voltammetry measurements were carried out and HOMO–LUMO energies were estimated. This study provides a starting point for the development of new poly(azomethine)s with doping‐dependent emission. © 2019 Society of Chemical Industry

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“…The π–π* red-shift combined with the larger CT intensity and its narrower broadening for Group A samples ( H1 , H3 , H4 and H6 ) is indicative of a lower molecule distortion, lower intermolecular interaction (no aggregation) and larger planarity that contribute to a decrease in the structural disorder of the material, compared to Group B compounds ( H2 and H5 ) [ 24 , 25 , 26 ]. Ellipsometric data have been confirmed by Raman measurements, as shown in Figure 7 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives

et al. 2022

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We have synthetized two classes of dibenzofulvene-arylamino derivatives with an H-shape design, for a total of six different molecules. The molecular structures consist of two D-A-D units connected by a thiophene or bitiophene bridge, using diarylamino substituents as donor groups anchored to the 2,7- (Group A) and 3,6- (Group B) positions of the dibenzofulvene backbone. The donor units and the thiophene or bithiophene bridges were used as chemico-structural tools to modulate electro-optical and morphological-electrical properties. A combination of experiments, such as absorption measurements (UV-Vis spectroscopy), cyclic voltammetry, ellipsometry, Raman, atomic force microscopy, TD-DFT calculation and hole-mobility measurements, were carried out on the synthesized small organic molecules to investigate the differences between the two classes and therefore understand the relevance of the molecular design of the various properties. We found that the anchoring position on dibenzofulvene plays a crucial key for fine-tuning the optical, structural, and morphological properties of molecules. In particular, molecules with substituents in 2,7 positions (Group A) showed a lower structural disorder, a larger molecular planarity, and a lower roughness.

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Electronic and structural properties of polymers based on phenylene vinylene and thiophene units. Control of the gap by gradual increases of thiophene moieties

Cited by 17 publications

References 37 publications

Design of Assembled Systems Based on Conjugated Polyphenylene Derivatives and Carbon Nanohorns

Design of Assembled Systems Based on Conjugated Polyphenylene Derivatives and Carbon Nanohorns

New cardo silylated poly(azomethine)s containing 9,9′‐diphenylfluorene units as materials with Brønsted acid‐dependent fluorescence

Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives

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