Supramolecular Assembly of Thiophene‐Based Oligomers into Nanostructured Fluorescent Conductive and Chiral Microfibers

Zangoli, Mattia; Maria, Francesca Di; Barbarella, Giovanna

doi:10.1002/open.201900347

Cited by 4 publications

(3 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All the modifications can thus influence the thiophene planarity and the electron density of the final products. Hence, a judicious selection of the synthetic substitution strategy may enable the design of a wide assortment of thiophene derivatives with bespoke physicochemical properties, and therefore, allowing to engineer a vast number of new thiophene-based molecules and materials with potential applicability in many fields of science and technology [37,38].…”

Section: Introductionmentioning

confidence: 99%

Thiophene-Based Covalent Organic Frameworks: Synthesis, Photophysics and Light-Driven Applications

2021

View full text Add to dashboard Cite

Porous crystalline materials, such as covalent organic frameworks (COFs), have emerged as some of the most important materials over the last two decades due to their excellent physicochemical properties such as their large surface area and permanent, accessible porosity. On the other hand, thiophene derivatives are common versatile scaffolds in organic chemistry. Their outstanding electrical properties have boosted their use in different light-driven applications (photocatalysis, organic thin film transistors, photoelectrodes, organic photovoltaics, etc.), attracting much attention in the research community. Despite the great potential of both systems, porous COF materials based on thiophene monomers are scarce due to the inappropriate angle provided by the latter, which hinders its use as the building block of the former. To circumvent this drawback, researchers have engineered a number of thiophene derivatives that can form part of the COFs structure, while keeping their intrinsic properties. Hence, in the present minireview, we will disclose some of the most relevant thiophene-based COFs, highlighting their basic components (building units), spectroscopic properties and potential light-driven applications.

show abstract

Section: Introductionmentioning

confidence: 99%

Thiophene-Based Covalent Organic Frameworks: Synthesis, Photophysics and Light-Driven Applications

2021

View full text Add to dashboard Cite

show abstract

“…Owing to the “plasticity” of the thiophene ring—imputable to the facile geometric deformability and adaptability of the ring to the environment, which is a consequence of the flexibility of the carbon‐sulfur bond—and its multiple nonbonding interactions, TpM can be organized in a wide variety of morphologies that enable a further tuning of their functionalities 21–24 . Recently, semiconducting polythiophene‐based nanoparticles (PT‐NPs), because of their excellent electron transport properties, high fluorescence, soft material nature, and water dispersibility, have been proved to have a huge potential in bioimaging and as nanoagents in photobiology 25–29 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and biological applications of semiconducting polythiophene‐based nanoparticles

Zangoli

Maria

2020

VIEW

Self Cite

View full text Add to dashboard Cite

In recent years, polythiophene‐based nanoparticles (PT‐NPs) have attracted increasing attention because of their outstanding characteristics deriving from a wealth of properties such as charge conduction in the oxidized/reduced states, light absorption/emission at an appropriate wavelength, geometrical adaptability, thermal and chemical stability, and solubility in common solvents. Furthermore, the great synthetic flexibility of the thiophene core has allowed the engineering of a multitude of nanomaterials with made‐to‐order properties. This review is focused on the synthesis and characterization of aqueous PT‐NPs and their biological applications. In particular, both in vitro and in vivo bioapplications will be presented, in which thiophene‐based nanomaterials act as photoactuators, that is, as exogenous components capable of transforming a primary stimulus of light into a highly spatiotemporally resolved secondary stimulus able to alter cell's physiological functions. Furthermore, examples of applications of PT‐NPs in biomedicine, such as photodynamic therapy and photothermal therapy, will be discussed.

show abstract

“…For this reason, the introduction of a heteroatom, such as sulfur or oxygen, between the thiophene ring and the chiral alkyl group should provide a reduction of the steric hindrance and promote conformations suitable to produce improved rings coplanarity with a longer extent of conjugation in the main chain, even in HH/TT regioregular polymeric derivatives. In addition, it is widely reported 12–19 that the presence of intramolecular interactions between the thienyl sulfur atom and the pendant sulfur or oxygen atom located in the adjacent moiety appears to provide a strong contribution to planarity of the backbone.…”

Section: Introductionmentioning

confidence: 99%

Effect of regioregularity and role of heteroatom on the chiral behavior of oligo(heteroalkyl thiophene)s

et al. 2020

Self Cite

View full text Add to dashboard Cite

Novel optically active oligothiophenes bearing electron‐donating chiral side chains have been prepared by synthetic methods suitable to achieve regioregular head‐to‐tail and head‐to‐head/tail‐to‐tail derivatives. In particular, the chiral (S)‐(2‐methyl)butyl moiety was linked at position 3 of the thiophene ring through heteroatoms, such as S or O, to evaluate its effect on the macro molecular aggregation and, consequently, on the chiroptical properties of the material in the solid state. The materials have been fully characterized and investigated by optical and chiroptical methods upon aggregation both from the solution and as cast films. Compared with the related head‐to‐tail and head‐to‐head/tail‐to‐tail poly(3‐alkyl)thiophene derivatives, with the same optically active moiety directly linked to the ring and possessing a higher polymerization degree, the chiroptical properties of the newly synthesized oligomers were significant, or even better, and provided insight into the role of intrachain–interchain interactions between the heteroatom and the thienyl sulfur atom.

show abstract

Supramolecular Assembly of Thiophene‐Based Oligomers into Nanostructured Fluorescent Conductive and Chiral Microfibers

Cited by 4 publications

References 49 publications

Thiophene-Based Covalent Organic Frameworks: Synthesis, Photophysics and Light-Driven Applications

Thiophene-Based Covalent Organic Frameworks: Synthesis, Photophysics and Light-Driven Applications

Synthesis, characterization, and biological applications of semiconducting polythiophene‐based nanoparticles

Effect of regioregularity and role of heteroatom on the chiral behavior of oligo(heteroalkyl thiophene)s

Contact Info

Product

Resources

About