Synthesis of d-glucose and l-phenylalanine substituted phenylene–thiophene oligomers

Omar, Omar Hassan; Babudri, Francesco; Farinola, Gianluca M.; Naso, Francesco; Operamolla, Alessandra; Pedone, Adriana

doi:10.1016/j.tet.2010.11.004

Cited by 16 publications

(5 citation statements)

References 61 publications

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“…In the synthesis of terthiophenes by Suzuki cross-coupling, a palladium complex catalyzes the C–C bond formation between a 2,5-dibromo- or 2,5-diiodothiophene and a thiophene boronic acid or boronate ester (pinacol ester) ( Scheme 5 ). The Suzuki reaction is today the most common choice for the synthesis of terthiophene derivatives, thanks to its good yield (50 to 90%) and to its compatibility with the presence of functional groups both on the thiophene halide and on the thiophene boronate [ 30 , 31 , 32 ]. After the discovery of this reaction in 1979, many studies assessed its ability to work for different heterocyclic compounds.…”

Section: Synthetic Methodologiesmentioning

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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Section: Synthetic Methodologiesmentioning

confidence: 99%

Thiophene-Based Trimers and Their Bioapplications: An Overview

et al. 2021

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“…Thiophene‐based oligo/polymers are one of the most interesting families of organic semiconducting materials for optoelectronic and nanotechnology applications 49–52 . For this reason, in recent years we have studied the aggregation modes in solution and thin films of several chiral thiophene‐based π‐conjugated dyes: (arylenethienylene)s with benzo[1,2‐ b :4,5‐ b ′]dithiophene, 53–55 1,4‐phenylene, 56–58 and 9 H ‐carbazole 59 central cores, bearing chiral appendages easily prepared in enantiopure form from natural sources (Figure 1A).…”

Section: Introductionmentioning

confidence: 99%

“…47,48 Thiophene-based oligo/polymers are one of the most interesting families of organic semiconducting materials for optoelectronic and nanotechnology applications. [49][50][51][52] For this reason, in recent years we have studied the aggregation modes in solution and thin films of several chiral thiophene-based π-conjugated dyes: (arylenethienylene)s with benzo[1,2-b:4,5-b 0 ]dithiophene, 53-55 1,4-phenylene, [56][57][58] and 9H-carbazole 59 central cores, bearing chiral appendages easily prepared in enantiopure form from natural sources (Figure 1A). In this article, we moved our attention onto oligothiophenes containing a 1,4-diketo-3,6-diarylpyrrolo [3,4-c]pyrrole (DPP) unit as the central core, decorated with chiral alkyl chains on the lactam nitrogen atoms, seeking their chiral aggregation modes in both solution and thin films by means of ECD spectroscopy (Figure 1B).…”

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Chiral diketopyrrolo[3,4‐c]pyrrole‐based oligothiophenes: Synthesis and characterization of aggregated states in solution and thin films

2023

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In this work, we synthesized a family of three structurally related chiral oligothiophenes containing a 1,4‐diketo‐3,6‐diarylpyrrolo[3,4‐c]pyrrole (DPP) unit as the central core; functionalized with the same (S)‐3,7‐dimethyl‐1‐octyl chains on the nitrogen atoms of lactam moieties, they only differ in the number of lateral thiophene units. The aggregation modes of these π‐conjugated chiral systems were evaluated by means of UV–Vis absorption and ECD spectroscopies in conditions of solution aggregation (CHCl3/MeOH mixtures) and as thin films, describing in particular the impact of the π‐conjugation length on the chiroptical properties. Interestingly, we found that the variable number of thiophene units attached to the DPP core affects not only the propensity to aggregation but also the aggregates' helicity. ECD revealed information about the supramolecular arrangement of these molecules, that one would not obtain by using conventional optical spectroscopy and microscopy techniques. Thin film samples revealed very different aggregation modes with respect to solution aggregates, casting doubts on the common assumption that these latter may serve as simple models of the former ones.

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“…The synthesis of these ternary components is simple and straightforward (see the Supporting Information for details). In addition, these two additives seemed ideal for our purpose because our past studies − have indicated the following: (i) 4T1B and 4T1BSAc display nearly identical energy levels (estimated from electrochemical and optical measurements, see Figures S11 and S12; data are summarized in Table ) that are in between those of P3HT and PC 60 BM and thus should lead to an energy-level cascade that can lead to efficient charge separation (Figure b/inset). (ii) They display a low tendency for resonant energy transfer in the ternary blend, due to the limited overlap between the solid state emission of P3HT and the additives’ absorption profile, and vice versa between the additives’ solid state emission and the absorption band of P3HT’s aggregated regions (see Figure S13).…”

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confidence: 99%