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

2021 ◽  
Vol 2 (2) ◽  
pp. 222-252
Author(s):  
Matías J. Alonso-Navarro ◽  
Elena Gala ◽  
M. Mar Ramos ◽  
Rocío Ponce Ortiz ◽  
José L. Segura
Keyword(s):  
Organic Semiconductors ◽  
Field Effect Transistors ◽  
Dipole Moments ◽  
Energy Levels ◽  
Aqueous Media ◽  
Morphological Characteristics ◽  
Force Microscopy ◽  
Macromolecular Systems ◽  
Donor Acceptor ◽  
Synthetic Approaches

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.

scholarly journals The Effect of Acceptor Structure on Emission Color Tuning in Organic Semiconductors with D–π–A–π–D Structures

Nanomaterials ◽  
2019 ◽  
Vol 9 (8) ◽  
pp. 1179 ◽  
Author(s):  
Przemyslaw Ledwon ◽  
Gabriela Wiosna-Salyga ◽  
Marian Chapran ◽  
Radoslaw Motyka
Keyword(s):  
Organic Semiconductors ◽  
Fluorescence Spectra ◽  
Near Infrared ◽  
Energy Levels ◽  
Light Emitting ◽  
Emission Color ◽  
Donor Acceptor ◽  
Homo And Lumo ◽  
Emission Quenching ◽  
Homo And Lumo Energy

A series of novel donor–acceptor D–π–A–π–D compounds were synthesized and characterized in order to determine the influence of different acceptor units on their properties. The introduction of acceptor moieties had a direct impact on the HOMO and LUMO energy levels. Fluorescence spectra of compounds can be changed by the choice of an appropriate acceptor and were shifted from the green to the near-infrared part of spectra. Due to observed concentration induced emission quenching, the green exciplex type host was used to evaluate the potential of synthesized molecules as emitters in organic light emitting diodes (OLEDs).

Electrochemistry, a Useful Tool in the Synthesis of Oligothiophenes

2021 ◽  
Vol 25 ◽  
Author(s):  
Fabiana Pandolfi ◽  
Martina Bortolami ◽  
Marta Feroci ◽  
Leonardo Mattiello ◽  
Vincenzo Scarano ◽  
...  
Keyword(s):  
Molecular Orbital ◽  
Organic Semiconductors ◽  
Organic Solar Cells ◽  
Field Effect Transistors ◽  
Energy Levels ◽  
Organic Field Effect Transistors ◽  
Light Emitting ◽  
Highest Occupied Molecular Orbital ◽  
Lowest Unoccupied Molecular Orbital ◽  
Organic Photodetectors

: Thiophene derivatives, either "small molecules," oligomers or polymers, play a role of primary importance among organic semiconductors. Therefore they have numerous and different technological applications in the field of Organic Electronics. For this reason, thiophene-based materials are found in devices such as organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), organic solar cells (OSCs), organic photodetectors, and many others. Oligothiophenes and polythiophenes have in common excellent charge transport properties and synthetic procedures that are now well established. Furthermore, oligothiophenes do not possess the intrinsic disadvantages of polythiophenes, such as the lack of well-defined structures and the inevitable presence of impurities. Electrochemistry can give a significant contribution to the field of oligothiophenes not only by allowing the determination of the highest-occupied molecular orbital (HOMO) and the lowest-unoccupied molecular orbital (LUMO) energy levels by the means of cyclic voltammetry (CV), but also rendering oligothiophenes syntheses more expeditious in comparison with the classical organic ones. This review outlines the application of electrochemistry techniques to the synthesis of oligothiophene derivatives.

scholarly journals Resolving Donor–Acceptor Interfaces and Charge Carrier Energy Levels of Organic Semiconductors with Polar Side Chains

2020 ◽  
Vol 30 (46) ◽  
pp. 2004799 ◽  
Author(s):  
Riccardo Alessandri ◽  
Selim Sami ◽  
Jonathan Barnoud ◽  
Alex H. Vries ◽  
Siewert J. Marrink ◽  
...  
Keyword(s):  
Charge Carrier ◽  
Organic Semiconductors ◽  
Energy Levels ◽  
Side Chains ◽  
Carrier Energy ◽  
Donor Acceptor

Theoretical Approach for the Development of Organic Semiconductors on the Basis of the MO Symmetry: Thienoacene as an Example

2012 ◽  
Vol 1436 ◽  
Author(s):  
Hirotaka Kojima ◽  
Takehiko Mori
Keyword(s):  
Organic Semiconductors ◽  
Field Effect ◽  
Field Effect Transistors ◽  
Theoretical Calculations ◽  
Energy Levels ◽  
Two Dimensional ◽  
Organic Field Effect Transistors ◽  
Transfer Integrals ◽  
Reorganization Energies ◽  
Herringbone Structure

ABSTRACTWe have explored materials for organic field-effect transistors (OFETs) from the viewpoint of theoretical calculations. The herringbone structure, which realizes two-dimensional conduction, is investigated in detail. Transfer integrals (t) are calculated systematically as a function of the dihedral angle between the molecular planes (θ) and the displacement along the molecular long axis (D). Acenes, oligothiophenes, thienoacenes and tetrathiafulvalenes are investigated, and are discussed from the molecular orbital (MO) symmetry. Thienoacenes (nTAs) are particularly examined as a candidate of OFET materials from the calculations of transfer integrals and reorganization energies (λ) based on the energy levels and the MO symmetry. LUMO of nTAs have MO symmetry suitable for conduction, but these orbitals are usually not related to the conduction. We have investigated the electronic properties of the derivatives with dicarboximide moiety. nTA-tetracarboxydiimide is expected to show the herringbone structure and exhibit n-type transport from the properties of LUMO.

scholarly journals Dithienylbenzothiadiazole-Based Donor-Acceptor Organic Semiconductors and Effect of End Capping Groups on Organic Field Effect Transistor Performance

2013 ◽  
Vol 66 (3) ◽  
pp. 370
Author(s):  
Prashant Sonar ◽  
Samarendra P. Singh ◽  
Ting Ting Lin ◽  
Ananth Dodabalapur
Keyword(s):  
Molecular Orbital ◽  
Organic Semiconductors ◽  
Field Effect ◽  
Carrier Mobility ◽  
Field Effect Transistor ◽  
Energy Levels ◽  
Lumo Energy ◽  
Donor Acceptor ◽  
Effect Transistor ◽  
End Capping

Donor-Acceptor-Donor (D-A-D) based conjugated molecules 4,7-bis(5-(4-butoxyphenyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole (BOP-TBT) and 4,7-bis(5-(4-trifluoromethyl)phenyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TFP-TBT) using thiophene-benzothiadiazole-thiophene central core with trifluoromethyl phenyl and butoxyphenyl end capping groups were designed and synthesised via Suzuki coupling. Optical, electrochemical, thermal, and organic field effect transistor (OFET) device properties of BOP-TBT and TFP-TBT were investigated. Both small molecules possess two absorption bands. Optical band gaps were calculated from the absorption cut off to be in the range of 2.06–2.25 eV. Cyclic voltammetry indicated reversible oxidation and reduction processes and the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels were calculated to be in the range of 5.15–5.40 eV and 3.25–3.62 eV, respectively. Upon testing both materials for OFET, trifluoromethylphenyl end capped material (TFP-TBT) shows n-channel behaviour whereas butoxyphenyl end capped material (BOP-TBT) shows p-channel behaviour. Density functional theory calculations correlated with shifting of HOMO-LUMO energy levels with respect to end capping groups. Vacuum processed OFET of these materials have shown highest hole carrier mobility of 0.02 cm2/Vs and electron carrier mobility of 0.004 cm2/Vs, respectively using Si/SiO2 substrate. By keeping the central D-A-D segment and just by tuning end capping groups gives both p- and n-channel organic semiconductors which can be prepared in a single step using straightforward synthesis.

scholarly journals Resolving Donor-Acceptor Interfaces and Charge Carrier Energy Levels of Organic Semiconductors with Polar Side Chains

2020 ◽  
Author(s):  
Riccardo Alessandri ◽  
Selim Sami ◽  
Jonathan Barnoud ◽  
Alex H. de Vries ◽  
Siewert-Jan Marrink ◽  
...  
Keyword(s):  
Charge Carrier ◽  
Organic Semiconductors ◽  
Large Scale ◽  
Energy Levels ◽  
Acid Methyl Ester ◽  
Side Chains ◽  
Organic Thin Film ◽  
Carrier Energy ◽  
Donor Acceptor ◽  
The Impact

<div> <div> <div> <p>Organic semiconductors consisting of molecules bearing polar side chains have been proposed as potential candidates to overcome the limitations of organic photovoltaics owing to their enhanced dielectric constant. However, introducing such polar molecules in photovoltaic devices has not yet resulted in higher efficiencies. A microscopic understanding of the impact of polar side chains on electronic and structural properties of organic semiconductors is paramount to rationalize their effect. Here, we investigate the impact of such side chains on bulk heterojunction overall morphology, molecular configurations at donor-acceptor (DA) interfaces, and charge carrier energy levels. The multiscale modeling approach used allows to resolve DA interfaces with atomistic resolution while taking into account the large-scale self-organization process which takes place during the processing of an organic thin film. The polar fullerene-based blends are compared to the well-studied reference system, poly(3-hexyl-thiophene) (P3HT):phenyl-C61-butyric acid methyl ester (PCBM). Introduction of polar side chains on a similar molecular scaffold does not affect molecular orientations at the DA interfaces; such orientations are however found to be affected by processing conditions and polymer molecular weight. Polar side chains, instead, are found to impact considerably the charge carrier energy levels of the organic blend, causing electrostatic-induced broadening of these levels. </p> </div> </div> </div>

scholarly journals Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors

Materials ◽  
2020 ◽  
Vol 13 (13) ◽  
pp. 3020
Author(s):  
Takato Asoh ◽  
Kohsuke Kawabata ◽  
Kazuo Takimiya
Keyword(s):  
Organic Semiconductors ◽  
Field Effect Transistors ◽  
Theoretical Calculations ◽  
Energy Levels ◽  
Hole Mobility ◽  
Hole Transport ◽  
Large Contribution ◽  
Theoretical Predictions ◽  
Reorganization Energies ◽  
P Type

A series of quinoidal oligothiophenes terminated with carbonyl groups (nTDs, n = 2–4) are studied as p-type organic semiconductors for the active materials in organic field-effect transistors (OFETs) both by the theoretical and experimental approaches. The theoretical calculations clearly show their high-lying highest occupied molecular orbital (HOMO) energy levels (EHOMOs), small reorganization energies for hole transport (λholes), and large contribution of sulfur atoms to HOMOs, all of which are desirable for p-type organic semiconductors. Thus, we synthesized nTDs from the corresponding aromatic oligothiophene precursors and then evaluated their physicochemical properties and structural properties. These experimental evaluations of nTDs nicely proved the theoretical predictions, and the largest 4TDs in the series (4,4′′′-dihexyl- and 3′,4,4″,4′′′-tetrahexyl-5H,5′′′H-[2,2′:5′,2″:5″,2′′′-quaterthiophene]-5,5′′′-dione) can afford solution-processed OFETs showing unipolar p-type behaviors and hole mobility as high as 0.026 cm2 V−1 s−1.

scholarly journals Resolving Donor-Acceptor Interfaces and Charge Carrier Energy Levels of Organic Semiconductors with Polar Side Chains

2020 ◽  
Author(s):  
Riccardo Alessandri ◽  
Selim Sami ◽  
Jonathan Barnoud ◽  
Alex H. de Vries ◽  
Siewert-Jan Marrink ◽  
...  
Keyword(s):  
Charge Carrier ◽  
Organic Semiconductors ◽  
Large Scale ◽  
Energy Levels ◽  
Acid Methyl Ester ◽  
Side Chains ◽  
Organic Thin Film ◽  
Carrier Energy ◽  
Donor Acceptor ◽  
The Impact

<div> <div> <div> <p>Organic semiconductors consisting of molecules bearing polar side chains have been proposed as potential candidates to overcome the limitations of organic photovoltaics owing to their enhanced dielectric constant. However, introducing such polar molecules in photovoltaic devices has not yet resulted in higher efficiencies. A microscopic understanding of the impact of polar side chains on electronic and structural properties of organic semiconductors is paramount to rationalize their effect. Here, we investigate the impact of such side chains on bulk heterojunction overall morphology, molecular configurations at donor-acceptor (DA) interfaces, and charge carrier energy levels. The multiscale modeling approach used allows to resolve DA interfaces with atomistic resolution while taking into account the large-scale self-organization process which takes place during the processing of an organic thin film. The polar fullerene-based blends are compared to the well-studied reference system, poly(3-hexyl-thiophene) (P3HT):phenyl-C61-butyric acid methyl ester (PCBM). Introduction of polar side chains on a similar molecular scaffold does not affect molecular orientations at the DA interfaces; such orientations are however found to be affected by processing conditions and polymer molecular weight. Polar side chains, instead, are found to impact considerably the charge carrier energy levels of the organic blend, causing electrostatic-induced broadening of these levels. </p> </div> </div> </div>

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