scholarly journals Structure prediction of N-heteroacenes as potential organic semiconductors

2014 ◽  
Vol 70 (a1) ◽  
pp. C1621-C1621
Author(s):  
Josh Campbell ◽  
Graeme Day
Keyword(s):  
Solid State ◽  
Charge Transport ◽  
Electronic Properties ◽  
Organic Semiconductors ◽  
Structure Prediction ◽  
Crystal Packing ◽  
Polyaromatic Hydrocarbons ◽  
Ring Structure ◽  
Inorganic Semiconductors ◽  
Nitrogen Substitution

Organic electronics offer exciting new alternatives to traditional inorganic devices based on advantages such as lower cost, ease of manufacture and flexibility. Small molecule semiconductors such as pentacene and rubrene are the focus of intense research due to performance approaching that of inorganic semiconductors. Charge transfer in polyaromatic hydrocarbons (PAHs) relies on the degree of π-conjugation and overlap of the π-systems of neighbouring molecules in the solid state. Small changes in the intermolecular interactions can lead to important changes in crystal packing and electronic properties. Thus, functionalization of PAHs is often used to improve their packing in the solid state. The addition of electronegative atoms into the ring system of pentacene has been proposed for improving stability while retaining attractive properties. [1] N-heteroacenes result from the substitution of nitrogen into the arene ring structure. The resulting potential for weak hydrogen bonding could direct coplanar molecular arrangements, sheet formation and favourable π-overlap for charge transport. Theoretical studies [2] have been carried out showing promising properties at the molecular level. As of yet no analysis of the solid state of these molecules has been performed to investigate how this substitution affects the packing and electronic properties. Here, we present the results of crystal structure prediction studies and calculation of charge transport properties aimed at understanding the influence of nitrogen substitution on the crystal packing of N-heteropentacenes and their performance as semiconducting materials.

Rational design and crystal structure prediction of ring-fused double-PDI compounds as n-channel organic semiconductors: a DFT study

2021 ◽  
Author(s):  
Suryakanti Debata ◽  
Smruti R. Sahoo ◽  
Rudranarayan Khatua ◽  
Sridhar Sahu
Keyword(s):  
Crystal Structure ◽  
Charge Transport ◽  
Organic Semiconductors ◽  
Structure Prediction ◽  
Rational Design ◽  
Molecular Design ◽  
Design Strategy ◽  
Dft Study ◽  
Crystal Structure Prediction ◽  
Model Compounds

In this study, we present an effective molecular design strategy to develop the n-type charge transport characteristics in organic semiconductors, using ring-fused double perylene diimides (DPDIs) as the model compounds.

Growth direction dependent separate-channel charge transport in organic weak charge-transfer co-crystal of anthracene-DTTCNQ

2022 ◽  
Author(s):  
Hui Jiang ◽  
Jun Ye ◽  
Peng Hu ◽  
Shengli Zhu ◽  
Yanqin Liang ◽  
...  
Keyword(s):  
Charge Transfer ◽  
Charge Transport ◽  
Electronic Properties ◽  
Single Crystals ◽  
Organic Semiconductors ◽  
Crystal Engineering ◽  
Molecular Crystal ◽  
Growth Direction ◽  
Weak Charge ◽  
Separate Channel

Co-crystallization is an efficient way of molecular crystal engineering to tune the electronic properties of organic semiconductors. In this work, we synthesized anthracene-4,8-bis(dicyanomethylene)4,8-dihydrobenzo[1,2-b:4,5-b’]-dithiophene (DTTCNQ) single crystals as a template to...

Benzo[1,2-b:6,5-b′]dithiophene(dithiazole)-4,5-dione derivatives: synthesis, electronic properties, crystal packing and charge transport

2013 ◽  
Vol 1 (7) ◽  
pp. 1467 ◽  
Author(s):  
Yulia A. Getmanenko ◽  
Marina Fonari ◽  
Chad Risko ◽  
Bhupinder Sandhu ◽  
Elena Galán ◽  
...  
Keyword(s):  
Charge Transport ◽  
Electronic Properties ◽  
Crystal Packing

scholarly journals Comparison of Charge Transport and Opto-Electronic Properties of Pyrene and Anthracene Derivatives For OLED Applications

2021 ◽  
Author(s):  
K. Uzun ◽  
S. Sayın ◽  
Ö. Tamer ◽  
U. Çevik
Keyword(s):  
Charge Transport ◽  
Electronic Properties ◽  
Organic Semiconductors ◽  
Organic Electronic Devices ◽  
Compound A ◽  
Compound C ◽  
Td Dft ◽  
Electronic Parameters ◽  
Anthracene Derivatives ◽  
Reorganization Energies

Abstract In this paper, three organic semiconductors which are 9-[(5-nitropyridin-2-aminoethyl)iminiomethyl]-anthracene( a )and Nꞌ -((pyren-4-yl)methylene)isonicotinohydrazide ( b ), and novel organic semiconductor N -(2-((pyren-4-yl)methyleneamino)ethyl)-5-nitropyridin-2-amine ( c ) have been prepared. Their structure have been assessed using NMR and elemental analysis techniques. While compound (a) and compound (c) have same wing unit ([(5-nitropyridin-2-aminoethyl) iminiomethyl]), compounds (b) and (c) have same core unit (5-nitropyridin-2-amine). Based upon TD-DFT and Marcus theories, we have explored the effect of molecular structure on the opto-electronic properties for OLED applications. Our results show that, wing units of molecules effects the opto-electronics properties a lot than core units. Such that, compounds (a) and (c) which have same wing unit, have been exhibited quite similar behaviours from points of both structural and opto-electronic parameters. Wheares, similar sitiation has not been observed for compounds (b) and (c) which have same core unit. More importantly accordingly our results, compounds (a) and (c) exhibit obvious advantages for organic electronic devices in terms of calculated opto-electronic and charge transport properties such as with better absorption and emission parameters, lower energy gaps and reorganization energies, higher charge mobility, etc.

Charge transport in organic semiconductors

2020 ◽  
pp. 171-292
Author(s):  
Stephen R. Forrest
Keyword(s):  
Charge Transport ◽  
Organic Semiconductors ◽  
Photonic Devices ◽  
Basic Principles ◽  
Inorganic Semiconductors ◽  
Charge Densities ◽  
Disordered Films ◽  
Inorganic Semiconductor ◽  
Background Charge ◽  
Almost All

In this chapter, the basic principles of the origins of transport levels and bands, charge conduction in disordered materials, and injection from contacts are introduced. Charge transport in organics is fundamentally different than in inorganic semiconductors due to narrow transport bands that, in general, lead to charge transport via hopping, resulting in carrier mobilities that are at most only a few cm2/V s. Processes of charge injection leading to space charge limited transport that defines the current vs. voltage characteristics of the materials are discussed. Methods of measuring mobility, background charge densities, and quantifying charge recombination are described. Doping of organics using both molecular and atomic species to modify their conductivity is also considered. The theory of transport in energetically and structurally disordered films is developed. The chapter closes by describing, from first principles, the theory of conduction over organic and organic/inorganic semiconductor heterojunctions that are used in almost all organic photonic devices.

Connecting molecule oxidation to single crystal structural and charge transport properties in rubrene derivatives

2014 ◽  
Vol 2 (21) ◽  
pp. 4147-4155 ◽  
Author(s):  
S. Uttiya ◽  
L. Miozzo ◽  
E. M. Fumagalli ◽  
S. Bergantin ◽  
R. Ruffo ◽  
...  
Keyword(s):  
Solid State ◽  
Single Crystal ◽  
Charge Transport ◽  
Transport Properties ◽  
Crystal Packing ◽  
Crystal Structural

Stable rubrene derivatives displaying the same crystal packing features as orthorhombic rubrene are synthesized and their solid state properties studied.

Herringbone to cofacial solid state packing via H-bonding in diketopyrrolopyrrole (DPP) based molecular crystals: influence on charge transport

2015 ◽  
Vol 51 (1) ◽  
pp. 97-100 ◽  
Author(s):  
Joydeep Dhar ◽  
Durga Prasad Karothu ◽  
Satish Patil
Keyword(s):  
Solid State ◽  
Charge Carrier ◽  
Charge Transport ◽  
Carrier Mobility ◽  
Crystal Packing ◽  
Molecular Crystals ◽  
Charge Carrier Mobility ◽  
Molecular Materials

A change in crystal packing from herringbone to cofacial via H-bonding improves charge carrier mobility in diketopyrrolopyrrole based molecular materials.

The Influence of Nitrogen Position on Charge Carrier Mobility in Enantiopure Aza[6]helicene Crystals

2018 ◽  
Author(s):  
Francesco Salerno ◽  
Beth Rice ◽  
Julia Schmidt ◽  
Matthew J. Fuchter ◽  
Jenny Nelson ◽  
...  
Keyword(s):  
Solid State ◽  
Charge Carrier ◽  
Carrier Mobility ◽  
Chemical Structure ◽  
Crystal Packing ◽  
Charge Carrier Mobility ◽  
Individual Factor ◽  
Charge Mobility ◽  
Order Of Magnitude ◽  
Small Change

<p>The properties of an organic semiconductor are dependent on both the chemical structure of the molecule involved, and how it is arranged in the solid-state. It is challenging to extract the influence of each individual factor, as small changes in the molecular structure often dramatically change the crystal packing and hence solid-state structure. Here, we use calculations to explore the influence of the nitrogen position on the charge mobility of a chiral organic molecule when the crystal packing is kept constant. The transfer integrals for a series of enantiopure aza[6]helicene crystals sharing the same packing were analysed in order to identify the best supramolecular motifs to promote charge carrier mobility. The regioisomers considered differ only in the positioning of the nitrogen atom in the aromatic scaffold. The simulations showed that even this small change in the chemical structure has a strong effect on the charge transport in the crystal, leading to differences in charge mobility of up to one order of magnitude. Some aza[6]helicene isomers that were packed interlocked with each other showed high HOMO-HOMO integrals (up to 70 meV), whilst molecules arranged with translational symmetry generally afforded the highest LUMO-LUMO integrals (40 - 70 meV). As many of the results are not intuitively obvious, a computational approach provides additional insight into the design of new semiconducting organic materials.</p>

Design and Synthesis of Two-Dimensional Covalent Organic Frameworks with Four-Arm Cores: Prediction of Remarkable Ambipolar Charge-Transport Properties

2019 ◽  
Author(s):  
Simil Thomas ◽  
Hong Li ◽  
Raghunath R. Dasari ◽  
Austin Evans ◽  
William Dichtel ◽  
...  
Keyword(s):  
Charge Transport ◽  
Organic Semiconductors ◽  
Density Functional ◽  
Polymer Networks ◽  
Two Dimensional ◽  
Covalent Organic Frameworks ◽  
X Ray Diffraction ◽  
Zinc Porphyrin ◽  
Design And Synthesis ◽  
Predicted Values

<p>We have considered three two-dimensional (2D) π-conjugated polymer networks (i.e., covalent organic frameworks, COFs) materials based on pyrene, porphyrin, and zinc-porphyrin cores connected <i>via</i> diacetylenic linkers. Their electronic structures, investigated at the density functional theory global-hybrid level, are indicative of valence and conduction bands that have large widths, ranging between 1 and 2 eV. Using a molecular approach to derive the electronic couplings between adjacent core units and the electron-vibration couplings, the three π-conjugated 2D COFs are predicted to have ambipolar charge-transport characteristics with electron and hole mobilities in the range of 65-95 cm<sup>2</sup>V<sup>-1</sup>s<sup>-1</sup>. Such predicted values rank these 2D COFs among the highest-mobility organic semiconductors. In addition, we have synthesized the zinc-porphyrin based 2D COF and carried out structural characterization via powder X-ray diffraction and surface area analysis, which demonstrates the feasability of these electroactive networks.</p>

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