An Ambipolar Peryleneamidine Monoimide-Fused Polythiophene with Narrow Band Gap

Blanco, Raúl; Gómez, Rafael; Seoane, Carlos; Segura, José L.; Mena‐Osteritz, Elena; Bäuerle, Peter

doi:10.1021/ol0706861

Cited by 41 publications

(36 citation statements)

References 20 publications

(14 reference statements)

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“…The cyclic voltammetry of perylenemonoimide moieties showed typical redox type behavior. Regardless of the thickness of the film on the electrode, peryleneamidine monoimide units were electroactive, which indicate a good delocalization of charges on the fully conjugated moieties, as well for the p-and n-doping [64]. It should be noted that in this case, the perinone group was not located in the main backbone of the conjugated polymer.…”

Section: Electrochemical Propertiesmentioning

confidence: 82%

“…It should be noted that substitution with tetra-phenoxy groups at the bay region induced a decrease in the electron-accepting properties due to their predominant electron-donating effects [62]. Use of perylene monoimide instead of 39 in the synthesis process shown in Figure 16 led to unsymmetrical perinones which can easily be obtained [33,43,44,63,64].…”

Section: Synthesismentioning

confidence: 99%

“…Bauerle and coll. [64] synthesized a molecule having perylenemonoimide moieties directly fused and conjugated to the terthiophene monomer using imidazo cycle. This molecule could be polymerized electrochemically giving an ambipolar polymer.…”

Section: Electrochemical Propertiesmentioning

confidence: 99%

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Perinone—New Life of an Old Molecule

Łapkowski

2021

Materials

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A review of publications on the synthesis and properties of a family of compounds called perinones was carried out. The basic molecule has been known for several decades mainly as a photostable pigment, and in recent years it has become increasingly used in organic electronics. This paper describes the methods of synthesis of low molecular weight compounds and polymers based on that molecule; the basic spectroscopic, photochemical, electrochemical and electronic properties important for the construction of organic electronics and optoelectronics devices are also discussed.

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Section: Electrochemical Propertiesmentioning

confidence: 82%

Section: Synthesismentioning

confidence: 99%

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Perinone—New Life of an Old Molecule

Łapkowski

2021

Materials

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“…Depending on the amine, several linear and branched alkyl chains of different lengths were introduced on the N-position, with the purpose of improving the solubility of the resulting material [ 383 , 387 , 388 , 389 ]. The pyrrole-dione group is also found on perylene-fused trimers [ 185 , 390 , 391 ].…”

Section: Trimer Structuresmentioning

confidence: 99%

Thiophene-Based Trimers and Their Bioapplications: An Overview

et al. 2021

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Certainly, the success of polythiophenes is due in the first place to their outstanding electronic properties and superior processability. Nevertheless, there are additional reasons that contribute to arouse the scientific interest around these materials. Among these, the large variety of chemical modifications that is possible to perform on the thiophene ring is a precious aspect. In particular, a turning point was marked by the diffusion of synthetic strategies for the preparation of terthiophenes: the vast richness of approaches today available for the easy customization of these structures allows the finetuning of their chemical, physical, and optical properties. Therefore, terthiophene derivatives have become an extremely versatile class of compounds both for direct application or for the preparation of electronic functional polymers. Moreover, their biocompatibility and ease of functionalization make them appealing for biology and medical research, as it testifies to the blossoming of studies in these fields in which they are involved. It is thus with the willingness to guide the reader through all the possibilities offered by these structures that this review elucidates the synthetic methods and describes the full chemical variety of terthiophenes and their derivatives. In the final part, an in-depth presentation of their numerous bioapplications intends to provide a complete picture of the state of the art.

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“…This family of oligothiophene-imidazole-rylenimide assemblies was designed with the aim to study the influence of different variables in OFET devices: (i) the effect of the length of the oligothiophene fragment on the charge transport characteristics, (ii) the effect of the replacement of some thiophene units by weaker electron donor benzene moieties and (iii) the effect of the lateral extension of the π-conjugated systems via naphthalene diimide vs. perylene diimide core interchange. This first-generation of organic semiconductors based on rylenimide-fused oligothiophene units was obtained by condensation between suitable diaminooligothiophene unit 2 and the corresponding monoanhydride monoimide derivative 1 or 3 as it is depicted in Scheme 1 [10][11][12]. An analogue of NDI-3T in which the central thiophene unit is replaced by a benzene moiety, NDI-Ph-T-Ph (Figure 2) was also obtained by following a similar synthetic procedure.…”

Section: Amidine-based Oligothiophene-rylenimide Semiconductorsmentioning

confidence: 99%

Oligothiophene-Naphthalimide Hybrids Connected through Rigid and Conjugated Linkers in Organic Electronics: An Overview

Alonso‐Navarro

Gala

Ramos

et al. 2021

Electronic Materials

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In this article, we summarize the synthetic approaches developed in our research groups during the last decade to efficiently tune the optical, electrochemical and morphological characteristics of oligothiophene–naphthalimide assemblies. Different variables were tuned in these organic semiconductors, such as the planarity and the length of their π-conjugated backbones, the topology and energy levels of the frontier molecular orbitals (HOMO and LUMO) and their molecular dipole moments. The tuning of these properties can be connected with the microstructure properties observed by atomic force microscopy (AFM) and X-ray diffraction (XRD) in thin films as well as with the performances in organic field-effect transistors (OFETs). The possibility of incorporating these donor-acceptor assemblies into macromolecular structures is also addressed, and some innovative applications for these macromolecular systems, such as the degradation of organic pollutants in aqueous media, are also presented.

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An Ambipolar Peryleneamidine Monoimide-Fused Polythiophene with Narrow Band Gap

Cited by 41 publications

References 20 publications

Perinone—New Life of an Old Molecule

Perinone—New Life of an Old Molecule

Thiophene-Based Trimers and Their Bioapplications: An Overview

Oligothiophene-Naphthalimide Hybrids Connected through Rigid and Conjugated Linkers in Organic Electronics: An Overview

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