Browse
Submit Data
Databases
API
Help

Dataset Information

29 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Enhancing electron affinity and tuning band gap in donor-acceptor organic semiconductors by benzothiadiazole directed C-H borylation.

ABSTRACT: Electrophilic borylation using BCl3 and benzothiadiazole to direct the C-H functionalisation of an adjacent aromatic unit produces fused boracyclic materials with minimally changed HOMO energy levels but significantly reduced LUMO energy levels. In situ alkylation and arylation at boron using Al(alkyl)3 or Zn(aryl)2 is facile and affords boracycles that possess excellent stability towards protic solvents, including water, and display large bathochromic shifts leading to far red/NIR emission in the solid state with quantum yields of up to 34%. Solution fabricated OLEDs with far red/NIR electroluminescence are reported with EQEs > 0.4%.

SUBMITTER: Crossley DL

PROVIDER: S-EPMC5666683 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Enhancing electron affinity and tuning band gap in donor-acceptor organic semiconductors by benzothiadiazole directed C-H borylation.

Crossley D L DL Cade I A IA Clark E R ER Escande A A Humphries M J MJ King S M SM Vitorica-Yrezabal I I Ingleson M J MJ Turner M L ML

Chemical science 20150612 9

Electrophilic borylation using BCl3 and benzothiadiazole to direct the C-H functionalisation of an adjacent aromatic unit produces fused boracyclic materials with minimally changed HOMO energy levels but significantly reduced LUMO energy levels. In situ alkylation and arylation at boron using Al(alkyl)3 or Zn(aryl)2 is facile and affords boracycles that possess excellent stability towards protic solvents, including water, and display large bathochromic shi ...[more]

PMID: 29142733

Similar Datasets

C-H Borylation/Cross-Coupling Forms Twisted Donor-Acceptor Compounds Exhibiting Donor-Dependent Delayed Emission.

Project description:Benzothiadiazole (BT) directed C-H borylation using BCl3 , followed by B-Cl hydrolysis and Suzuki-Miyaura cross-coupling enables facile access to twisted donor-acceptor compounds. A subsequent second C-H borylation step provides, on arylation of boron, access to borylated highly twisted D-A compounds with a reduced bandgap, or on B-Cl hydrolysis/cross-coupling to twisted D-A-D compounds. Photophysical studies revealed that in this series there is long lifetime emission only when the donor is triphenylamine. Computational studies indicated that the key factor in observing the donor dependent long lifetime emission is the energy gap between the S1 /T2 excited states, which are predominantly intramolecular charge-transfer states, and the T1 excited state, which is predominantly a local excited state on the BT acceptor moiety.

| S-EPMC6099339 | biostudies-literature

Hydrogen production by tuning the photonic band gap with the electronic band gap of TiO?.

Project description:Tuning the photonic band gap (PBG) to the electronic band gap (EBG) of Au/TiO2 catalysts resulted in considerable enhancement of the photocatalytic water splitting to hydrogen under direct sunlight. Au/TiO2 (PBG-357 nm) photocatalyst exhibited superior photocatalytic performance under both UV and sunlight compared to the Au/TiO2 (PBG-585 nm) photocatalyst and both are higher than Au/TiO2 without the 3 dimensionally ordered macro-porous structure materials. The very high photocatalytic activity is attributed to suppression of a fraction of electron-hole recombination route due to the co-incidence of the PBG with the EBG of TiO2 These materials that maintain their activity with very small amount of sacrificial agents (down to 0.5 vol.% of ethanol) are poised to find direct applications because of their high activity, low cost of the process, simplicity and stability.

| S-EPMC3794377 | biostudies-literature

Facile band gap tuning in graphene-brucite heterojunctions.

Project description:The zero band gap of pure graphene is a well-known issue that limits some specific applications of graphene in opto- and microelectronics. This led to several research studies in the so-called van der Waals composites (known as heterostructures, or heterojunctions), where two monolayers of different materials are stacked and held together by dispersive interactions. In this paper, we introduced and considered a single layer of brucite Mg(OH)2, an overlooked 2D material that can be easily produced by exfoliation (like graphene from graphite), for the creation of the heterojunction. First principles simulations showed that brucite/graphene composites can modify the electronic properties (position of the Dirac cone with respect to the Fermi level and band gap) according to the crystallographic stacking and the presence of point defects. The present work represents then an important step forward in understanding and finding new ways to design two-dimensional materials with tailored electronic and physical properties.

| S-EPMC10754930 | biostudies-literature

Low Band Gap Donor⁻Acceptor Type Polymers Containing 2,3-Bis(4-(decyloxy)phenyl)pyrido[4,3-b]pyrazine as Acceptor and Different Thiophene Derivatives as Donors.

Project description:Four donor⁻acceptor type conducting polymers, namely poly(2,3-bis(4-decyloxy)phenyl)-5,8-bis(4-thiophen-2-yl)pyrido[4,3-b]pyrazine) (P1), poly(2,3-bis(4-decyloxy)phenyl)-5,8-bis(4-butylthiophen-2-yl)pyrido[4,3-b]pyrazine) (P2), poly(2,3-bis(4-(decyloxy)phenyl)-5,8-bis(4-hexyloxythiophen-2-yl)pyrido[4,3-b]pyrazine) (P3) and poly(2,3-bis(4-(decyloxy)phenyl)-5,8-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)pyrido[4,3-b]pyrazine) (P4), containing thiophene or its derivative as the donor and pyrido[4,3-b]pyrazine as the acceptor were prepared and characterized by cyclic voltammetry, scanning electron microscopy, and UV-Vis spectroscopy to detect the influence of the donor units' strength on the electrochromic performances. The results demonstrated that all of the polymers could be reversibly reduced and oxidized by p-type doping and n-type doping, and showed near-infrared activities and different color changes in p-type doping process. Especially, P3 and P4 showed lower optical band gap than P1 and P2 due to the strong electron-donating hexyloxythiophen group of P3 and ethylenedioxythiophene group of P4. Besides, P3 and P4 displayed the saturated green color at the neutral state and the desirable transparency at the oxidized state. All the polymers displayed desirable optical contrasts, satisfactory coloration efficiency, excellent stability and short switching time, which made the polymers fascinating candidates in the electrochromic device applications.

| S-EPMC6432059 | biostudies-literature

Highly Emissive Far Red/Near-IR Fluorophores Based on Borylated Fluorene-Benzothiadiazole Donor-Acceptor Materials.

Project description:Stille, Suzuki-Miyaura and Negishi cross-coupling reactions of bromine-functionalised borylated precursors enable the facile, high yielding, synthesis of borylated donor-acceptor materials that contain electron-rich aromatic units and/or extended effective conjugation lengths. These materials have large Stokes shifts, low LUMO energies, small band-gaps and significant fluorescence emission >700 nm in solution and when dispersed in a host polymer.

| S-EPMC6680280 | biostudies-literature

Triplet excited state properties in variable gap ?-conjugated donor-acceptor-donor chromophores.

Project description:A series of variable band-gap donor-acceptor-donor (DAD) chromophores capped with platinum(ii) acetylide units has been synthesized and fully characterized by electrochemical and photophysical methods, with particular emphasis placed on probing triplet excited state properties. A counter-intuitive trend of increasing fluorescence quantum efficiency and lifetime with decreasing excited state energy (optical gap) is observed across the series of DAD chromophores. Careful study of the excited state dynamics, including triplet yields (as inferred from singlet oxygen sensitization), reveals that the underlying origin of the unusual trend in the fluorescence parameters is that the singlet-triplet intersystem crossing rate and yield decrease with decreasing optical gap. It is concluded that the rate of intersystem crossing decreases as the LUMO is increasingly localized on the acceptor unit in the DAD chromophore, and this result is interpreted as arising because the extent of spin-orbit coupling induced by the platinum heavy metal centers decreases as the LUMO is more localized on the acceptor. In addition to the trend in intersystem crossing, the results show that the triplet decay rates follow the Energy Gap Law correlation over a 1.8 eV range of triplet energy and 1000-fold range of triplet decay rates. Finally, femtosecond transient absorption studies for the DAD chromophores reveals a strong absorption in the near-infrared region which is attributed to the singlet excited state. This spectral band appears to be general for DAD chromophores, and may be a signature of the charge transfer (CT) singlet excited state.

| S-EPMC6008705 | biostudies-other

Controlling n-Type Molecular Doping via Regiochemistry and Polarity of Pendant Groups on Low Band Gap Donor-Acceptor Copolymers.

Project description:We demonstrate the impact of the type and position of pendant groups on the n-doping of low-band gap donor-acceptor (D-A) copolymers. Polar glycol ether groups simultaneously increase the electron affinities of D-A copolymers and improve the host/dopant miscibility compared to nonpolar alkyl groups, improving the doping efficiency by a factor of over 40. The bulk mobility of the doped films increases with the fraction of polar groups, leading to a best conductivity of 0.08 S cm-1 and power factor (PF) of 0.24 μW m-1 K-2 in the doped copolymer with the polar pendant groups on both the D and A moieties. We used spatially resolved absorption spectroscopy to relate commensurate morphological changes to the dispersion of dopants and to the relative local doping efficiency, demonstrating a direct relationship between the morphology of the polymer phase, the solvation of the molecular dopant, and the electrical properties of doped films. Our work offers fundamental new insights into the influence of the physical properties of pendant chains on the molecular doping process, which should be generalizable to any molecularly doped polymer films.

| S-EPMC8154869 | biostudies-literature

Solution-Processed Donor-Acceptor Polymer Nanowire Network Semiconductors For High-Performance Field-Effect Transistors.

Project description:Organic field-effect transistors (OFETs) represent a low-cost transistor technology for creating next-generation large-area, flexible and ultra-low-cost electronics. Conjugated electron donor-acceptor (D-A) polymers have surfaced as ideal channel semiconductor candidates for OFETs. However, high-molecular weight (MW) D-A polymer semiconductors, which offer high field-effect mobility, generally suffer from processing complications due to limited solubility. Conversely, the readily soluble, low-MW D-A polymers give low mobility. We report herein a facile solution process which transformed a lower-MW, low-mobility diketopyrrolopyrrole-dithienylthieno[3,2-b]thiophene (I) into a high crystalline order and high-mobility semiconductor for OFETs applications. The process involved solution fabrication of a channel semiconductor film from a lower-MW (I) and polystyrene blends. With the help of cooperative shifting motion of polystyrene chain segments, (I) readily self-assembled and crystallized out in the polystyrene matrix as an interpenetrating, nanowire semiconductor network, providing significantly enhanced mobility (over 8?cm(2)V(-1)s(-1)), on/off ratio (10(7)), and other desirable field-effect properties that meet impactful OFET application requirements.

| S-EPMC4835732 | biostudies-literature

Electronically Driven Regioselective Iridium-Catalyzed C-H Borylation of Donor-?-Acceptor Chromophores Containing Triarylboron Acceptors.

Project description:We observed a surprisingly high electronically driven regioselectivity for the iridium-catalyzed C-H borylation of donor-?-acceptor (D-?-A) systems with diphenylamino (1) or carbazolyl (2) moieties as the donor, bis(2,6-bis(trifluoromethyl)phenyl)boryl (B(F Xyl)2 ) as the acceptor, and 1,4-phenylene as the ?-bridge. Under our conditions, borylation was observed only at the sterically least encumbered para-positions of the acceptor group. As boronate esters are versatile building blocks for organic synthesis (C-C coupling, functional group transformations) the C-H borylation represents a simple potential method for post-functionalization by which electronic or other properties of D-?-A systems can be fine-tuned for specific applications. The photophysical and electrochemical properties of the borylated (1-(Bpin)2 ) and unborylated (1) diphenylamino-substituted D-?-A systems were investigated. Interestingly, the borylated derivative exhibits coordination of THF to the boronate ester moieties, influencing the photophysical properties and exemplifying the non-innocence of boronate esters.

| S-EPMC7497074 | biostudies-literature

Tuning band gap and enhancing optical functions of AGeF3 (A = K, Rb) under pressure for improved optoelectronic applications.

Project description:The current study diligently analyzes the physical characteristics of halide perovskites AGeF3 (A = K, Rb) under hydrostatic pressure using density functional theory. The goal of this research is to reduce the electronic band gap of AGeF3 (A = K, Rb) under pressure in order to improve the optical characteristics and assess the compounds' suitability for optoelectronic applications. The structural parameters exhibit a high degree of precision, which correlates well with previously published work. In addition, the bond length and lattice parameters decrease significantly leading to a stronger interaction between atoms. The bonding between K(Rb)-F and Ge-F reveal ionic and covalent nature, respectively, and the bonds become stronger under pressure. The application of hydrostatic pressure demonstrates remarkable changes in the optical absorption and conductivity. The band gap becomes lower with the increment of pressure, resulting in better conductivity. The optical functions also predict that the studied materials might be used in a variety of optoelectronic devices operating in the visible and ultraviolet spectrum. Interestingly, the compounds become more suitable to be used in optoelectronic applications under pressure. Moreover, the external pressure has profound dominance on the mechanical behavior of the titled perovskites, which make them more ductile and anisotropic.

| S-EPMC9126918 | 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