Browse
Submit Data
Databases
API
Help

Dataset Information

29 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Extended 2,2'-Bipyrroles: New Monomers for Conjugated Polymers with Tailored Processability.

ABSTRACT: The synthesis of 2,2'-bipyrroles substituted at positions 5,5' with pyrrolyl, N-methyl-pyrrolyl and thienyl groups and their application in the preparation of conducting polymers is reported herein. The preparation of these monomers consisted of two synthetic steps from a functionalized 2,2'-bipyrrole: Bromination of the corresponding 2,2'-bipyrrole followed by Suzuki or Stille couplings. These monomers display low oxidation potential compared to pyrrole because of the extended length of their conjugation pathway. The resulting monomers can be polymerized through oxidative/electropolymerization. Electrical conductivity and electrochromic properties of the electrodeposited polymeric films were evaluated using 4-point probe measurements and cyclic voltammetry to evaluate their applicability in electronics.

SUBMITTER: Texido R

PROVIDER: S-EPMC6630584 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Extended 2,2'-Bipyrroles: New Monomers for Conjugated Polymers with Tailored Processability.

Texidó Robert R Anguera Gonzalo G Colominas Sergi S Borrós Salvador S Sánchez-García David D

Polymers 20190620 6

The synthesis of 2,2'-bipyrroles substituted at positions 5,5' with pyrrolyl, <i>N</i>-methyl-pyrrolyl and thienyl groups and their application in the preparation of conducting polymers is reported herein. The preparation of these monomers consisted of two synthetic steps from a functionalized 2,2'-bipyrrole: Bromination of the corresponding 2,2'-bipyrrole followed by Suzuki or Stille couplings. These monomers display low oxidation potential compared to pyrrole because of the extended length of ...[more]

PMID: 31226800

Similar Datasets

Dynamics of Photoinduced Energy Transfer in Fully and Partially Conjugated Polymers Bearing π-Extended Donor and Acceptor Monomers.

Project description:The photophysical properties of donor (D)-acceptor (A) polymers were studied by designing two types of polymers, (D-σ-A) n and (D-π-A) n , with non-conjugated alkyl (sp 3) and π-conjugated (sp 2) linkers using π-extended donor and acceptor monomers that exhibit planar A-D-A structures. The non-conjugated alkyl linker provides structural flexibility to the (D-σ-A) n polymers, while the π-conjugated linker retains the rigid structure of the (D-π-A) n polymers. Photoinduced energy transfer occurs from the large donor to acceptor units in both polymers. However, the photoinduced energy transfer dynamics are found to be dependent on the conformation of the polymers, where the difference is dictated by the types of linkers between the donor and acceptor units. In solution, intramolecular energy transfer is relatively favorable for the (D-σ-A) n polymers with flexible linkers that allow the donor and acceptor units to be proximally located in the polymers. On the other hand, intermolecular (or interchain) energy transfer is dominant in the two polymer films because the π-extended donor and acceptor units in polymers are closely packed. The structural flexibility of the linkers between the donor and acceptor repeating units in the polymers affects the efficiency of energy transfer between the donor and acceptor units and the overall photophysical properties of the polymers.

| S-EPMC7674937 | biostudies-literature

Influence of Regioregularity on the Optoelectronic Properties of Conjugated Diketopyrrolopyrrole Polymers Comprising Asymmetric Monomers.

Project description:Two asymmetric thiophene (T)/pyridine (Py) flanked diketopyrrolopyrrole (DPP) polymers with a regiorandom and regioregular conjugated backbone are synthesized via a Stille polycondensation to investigate the effect of regioregularity on their optoelectronic properties and photovoltaic performance in fullerene-based polymer solar cells. Surprisingly, both polymers possess very similar optical bandgap, energy levels, and photovoltaic performance. These findings, combined with a factor of 19 reactivity difference between the two end groups of the asymmetric DPP monomer, intuitively suggest the formation of regular chain segments in the random polymer. However, by modeling the random polymerization reaction with a kinetic Monte Carlo (KMC) simulation, evidence is obtained for exclusive formation of a fully random polymer structure. UV-vis-NIR absorption spectra of three extended DPP chromophores, containing the donor segments (T-T-T, Py-T-Py, and Py-T-T) present in the regiorandom polymer, confirm that regioregularity of the backbone has a negligible influence on the optical properties.

| S-EPMC7513466 | biostudies-literature

Synthesis of Conjugated Polymers Containing B←N Bonds with Strong Electron Affinity and Extended Absorption.

Project description:The B←N is isoelectronic to the C-C, with the former having stronger dipole moment and higher electron affinity. Replacing the C-C bonds in conjugated polymers with B←N bonds is an effective pathway toward novel polymers with strong electron affinity and adjustable optoelectronic properties. In this work, we synthesize a conjugated copolymer, namely, BNIDT-DPP, based on a B←N embedded unit, BNIDT, and a typical electron-deficient unit, diketopyrrolopyrrole (DPP). For comparison, the C-C counterpart, i.e., IDT-DPP, is also synthesized. In contrast to IDT-DPP, the B←N embedded polymer BNIDT-DPP shows an extended absorption edge (836 versus 978 nm), narrowed optical bandgap (1.48 versus 1.27 eV), and higher electron affinity (3.54 versus 3.74 eV). The Gaussian simulations reveal that the B←N embedded polymer BNIDT-DPP is more electron-deficient in contrast to IDT-DPP, supporting the decreased bandgap and energy levels of BNIDT-DPP. Organic thin-film transistor (OTFT) tests indicate a well-defined p-type characteristic for both IDT-DPP and BNIDT-DPP. The hole mobilities of IDT-DPP and BNIDT-DPP tested by OTFTs are 0.059 and 0.035 cm2/V·s, respectively. The preliminary fabrication of all-polymer solar cells based on BNIDT-DPP and PBDB-T affords a PCE of 0.12%. This work develops a novel B←N embedded polymer with strong electron affinity and extended absorption, which is potentially useful for electronic device application.

| S-EPMC6835370 | biostudies-literature

Exploiting coordination geometry to tune the dimensions and processability of metallosupramolecular polymers.

Project description:Achieving precise control over the morphology, dimensions and processability of functional materials is a key but challenging requirement for the fabrication of smart devices. To address this issue, we herein compare the self-assembly behavior of two new Pt(ii) complexes that differ in the molecular and coordination geometry through implementation of either a monodentate (pyridine) or bidentate (bipyridine) ligand. The molecular preorganization of the bipyridine-based complex enables effective self-assembly in solution involving Pt⋯Pt interactions, while preserving aggregate solubility. On the other hand, increased steric effects of the linear bispyridine-based complex hinder an effective preorganization leading to poorly solvated aggregates when a critical concentration is exceeded.

| S-EPMC8314868 | biostudies-literature

New insights into the design of conjugated polymers for intramolecular singlet fission.

Project description:Singlet fission (SF), a multiple exciton generation process that generates two triplet excitons after the absorption of one photon, can potentially enable more efficient solar cell designs by harvesting energy normally lost as heat. While low-bandgap conjugated polymers are highly promising candidates for efficient SF-based solar cells, few polymer materials capable of SF have been reported because the SF process in polymer chains is poorly understood. Using transient spectroscopy, we demonstrate a new, highly efficient (triplet yield of 160-200%) isoindigo-based donor-acceptor polymer and show that the triplet pairs are directly emissive and exhibit a time-dependent energy evolution. Importantly, aggregation in poor solvents and in films significantly lowers the singlet energy, suppressing triplet formation because the energy conservation criterion is no longer met. These results suggest a new design rule for developing intramolecular SF capable low-bandgap conjugated polymers, whereby inter-chain interactions must be carefully engineered.

| S-EPMC6068183 | biostudies-literature

Advances in Conjugated Microporous Polymers.

Project description:Conjugated microporous polymers (CMPs) are a unique class of materials that combine extended ?-conjugation with a permanently microporous skeleton. Since their discovery in 2007, CMPs have become established as an important subclass of porous materials. A wide range of synthetic building blocks and network-forming reactions offers an enormous variety of CMPs with different properties and structures. This has allowed CMPs to be developed for gas adsorption and separations, chemical adsorption and encapsulation, heterogeneous catalysis, photoredox catalysis, light emittance, sensing, energy storage, biological applications, and solar fuels production. Here we review the progress of CMP research since its beginnings and offer an outlook for where these materials might be headed in the future. We also compare the prospect for CMPs against the growing range of conjugated crystalline covalent organic frameworks (COFs).

| S-EPMC7145355 | biostudies-literature

Sequencing conjugated polymers by eye.

Project description:The solid-state microstructure of a conjugated polymer is the most important parameter determining its properties and performance in (opto)-electronic devices. A huge amount of research has been dedicated to tuning and understanding how the sequence of monomers, the nature and frequency of defects, the exact backbone conformation, and the assembly and crystallinity of conjugated polymers affect their basic photophysics and charge transporting properties. However, because of the lack of reliable high-resolution analytical techniques, all the structure-property relations proposed in the literature are based either on molecular modeling or on indirect experimental data averaged on polydisperse samples. We show that a combination of electrospray vacuum deposition and high-resolution scanning tunneling microscopy allows the imaging of individual conjugated polymers with unprecedented detail, thereby unraveling structural and self-assembly characteristics that have so far been impossible to determine.

| S-EPMC6003723 | biostudies-literature

Synthesis and characterization of aryl thioacetyl styrene monomers: Towards a new generation of SERS-active polymers.

Project description:A new family of thioacetyl styrene derivatives was synthesized in good isolated yields for the preparation of spectroscopically-encoded SERS-active polymers.

| S-EPMC2180836 | biostudies-literature

Two-dimensional polymers with versatile functionalities via gemini monomers.

Project description:Two-dimensional synthetic polymers (2DSPs) are sheet-like macromolecules consisting of covalently linked repeat units in two directions. Access to 2DSPs with controlled size and shape and diverse functionality has been limited because of the need for monomers to retain their crystallinity throughout polymerization. Here, we describe a synthetic strategy for 2DSPs that obviates the need for crystallinity, via the free radical copolymerization of amphiphilic gemini monomers and their monomeric derivatives arranged in a bilayer at solid-liquid interfaces. The ease of this strategy allowed the preparation of 2DSPs with well-controlled size and shape and diverse functionality on solid templates composed of various materials with wide-ranging surface curvatures and dimensions. The resulting 2DSPs showed remarkable mechanical strength and have multiple applications, such as nanolithographic resist and antibacterial agent. The broad scope of this approach markedly expands the chemistry, morphology, and functionality of 2DSPs accessible for practical applications.

| S-EPMC6874491 | biostudies-literature

Novel Mesogenic Vinyl Ketone Monomers and Their Based Polymers.

Project description:In the present research, we have synthesized new vinyl ketone monomers with mesogenic substituents, namely, 8-(3'-chloro-4'-pentyl-[1,1'-biphenyl-4-oxy)oct-1-en-3-one (BVK) and 8-[2'-chloro-4‴-octyl-[1,1':4',1″:4″,1‴-quaterphenyl-4-oxy]oct-1-en-3-one (QVK). The comparison of BVK, QVK, and previously synthesized 8-((4″-((1R,4S)-4-butylcyclohexyl)-2'-chloro-[1,1',4',1″-terphenyl]-4-yl)oxy)oct-1-en-3-one (TVK) has revealed that all of them are able to form crystals, while their ability to exhibit liquid crystalline behavior depends on the number of phenyl substituents attached to the para-position of the phenoxy group and is observed for TVK and QVK only. All of the monomers are able to achieve self-polymerization upon heating and free radical polymerization in bulk or in solution under the action of the common radical initiator AIBN. We have also succeeded in the RAFT polymerization of the synthesized vinyl ketones BVK and TVK using asymmetrical trithiocarbonates. The synthesized poly(vinyl ketones) exhibit LC behavior and are able to undergo photodegradation upon UV irradiation.

| S-EPMC9823505 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data