Molecular Tetrominoes: Selective Masking of Donor pi-face to Control Configuration of Donor-Acceptor Complex

Understanding the doping mechanism in organic semiconductors and generating molecular design rules to control the doping process is crucial to improve the performance of organic electronics. Even though controlling the...

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Constructing Donor-Resonance-Donor Molecules for Acceptor-Free Bipolar Organic Semiconductors

Research ◽

10.34133/2021/9525802 ◽

2021 ◽

Vol 2021 ◽

pp. 1-10

Author(s):

He Jiang ◽

Jibiao Jin ◽

Zijie Wang ◽

Wuji Wang ◽

Runfeng Chen ◽

...

Keyword(s):

Organic Semiconductors ◽

High Performance ◽

Molecular Design ◽

Stimuli Responsive ◽

Light Emitting ◽

Deep Blue ◽

Device Structures ◽

Device Applications ◽

Donor Acceptor ◽

Organic Optoelectronic

Organic semiconductors with bipolar transporting character are highly attractive as they offer the possibility to achieve high optoelectronic performance in simple device structures. However, the continual efforts in preparing bipolar materials are focusing on donor-acceptor (D-A) architectures by introducing both electron-donating and electron-withdrawing units into one molecule in static molecular design principles. Here, we report a dynamic approach to construct bipolar materials using only electron-donating carbazoles connected by N-P=X resonance linkages in a donor-resonance-donor (D-r-D) structure. By facilitating the stimuli-responsive resonance variation, these D-r-D molecules exhibit extraordinary bipolar properties by positively charging one donor of carbazole in enantiotropic N+=P-X- canonical forms for electron transport without the involvement of any acceptors. With thus realized efficient and balanced charge transport, blue and deep-blue phosphorescent organic light emitting diodes hosted by these D-r-D molecules show high external quantum efficiencies up to 16.2% and 18.3% in vacuum-deposited and spin-coated devices, respectively. These results via the D-r-D molecular design strategy represent an important concept advance in constructing bipolar organic optoelectronic semiconductors dynamically for high-performance device applications.

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High Temperature Organic Electronics

MRS Advances ◽

10.1557/adv.2020.31 ◽

2020 ◽

Vol 5 (10) ◽

pp. 505-513

Author(s):

Aristide Gumyusenge ◽

Jianguo Mei

Keyword(s):

High Temperature ◽

Organic Semiconductors ◽

Organic Electronics ◽

Elevated Temperatures ◽

Molecular Design ◽

State Of The Art ◽

Stable Operation ◽

High Temperature Electronics ◽

New Class ◽

Review Current

ABSTRACTThe emerging breakthroughs in space exploration, smart textiles, and novel automobile designs have increased technological demand for high temperature electronics. In this snapshot review we first discuss the fundamental challenges in achieving electronic operation at elevated temperatures, briefly review current efforts in finding materials that can sustain extreme heat, and then highlight the emergence of organic semiconductors as a new class of materials with potential for high temperature electronics applications. Through an overview of the state-of-the art materials designs and processing methods, we will layout molecular design principles and fabrication strategies towards achieving thermally stable operation in organic electronics.

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Energetic Control of Redox-Active Polymers Towards Safe Organic Bioelectronic Materials

10.26434/chemrxiv.11366186.v1 ◽

2019 ◽

Author(s):

Alexander Giovannitti ◽

Reem B. Rashid ◽

Quentin Thiburce ◽

Bryan D. Paulsen ◽

Camila Cendra ◽

...

Keyword(s):

Molecular Oxygen ◽

Organic Semiconductors ◽

Side Reaction ◽

Semiconducting Polymers ◽

Side Reactions ◽

Redox Active ◽

Donor Acceptor ◽

Electrochemical Devices ◽

Biological Environment ◽

Device Operation

Avoiding faradaic side reactions during the operation of electrochemical devices is important to enhance the device stability, to achieve low power consumption, and to prevent the formation of reactive side‑products. This is particularly important for bioelectronic devices which are designed to operate in biological systems. While redox‑active materials based on conducting and semiconducting polymers represent an exciting class of materials for bioelectronic devices, they are susceptible to electrochemical side‑reactions with molecular oxygen during device operation. We show that this electrochemical side reaction yields hydrogen peroxide (H2O2), a reactive side‑product, which may be harmful to the local biological environment and may also accelerate device degradation. We report a design strategy for the development of redox-active organic semiconductors based on donor-acceptor copolymers that prevent the formation of H2O2 during device operation. This study elucidates the previously overlooked side-reactions between redox-active conjugated polymers and molecular oxygen in electrochemical devices for bioelectronics, which is critical for the operation of electrolyte‑gated devices in application-relevant environments.

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Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

10.26434/chemrxiv.11912073 ◽

2020 ◽

Author(s):

José Tiago Menezes Correia ◽

Gustavo Piva da Silva ◽

Camila Menezes Kisukuri ◽

Elias André ◽

Bruno Pires ◽

...

Keyword(s):

Electron Donor ◽

Functional Group ◽

Photoexcited Electron ◽

One Pot ◽

Quaternary Centers ◽

Metal Free ◽

Acceptor Complex ◽

Catalyst Free ◽

Donor Acceptor ◽

Radical Cascade

A metal- and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donor-aceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. <a>The method provides an operationally simple, robust and step-economical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential one-pot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches</a>.

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

Physical Chemistry Chemical Physics ◽

10.1039/d1cp00008j ◽

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.

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Donor–Acceptor Complex Enables Cascade Radical Cyclization of N-Arylacrylamides with Katritzky Salts

Organic Letters ◽

10.1021/acs.orglett.1c01758 ◽

2021 ◽

Author(s):

Yu Lu ◽

Chang-Zhen Fang ◽

Qiang Liu ◽

Bao-Lin Li ◽

Zhi-Xiang Wang ◽

...

Keyword(s):

Radical Cyclization ◽

Acceptor Complex ◽

Donor Acceptor

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Synthesis and Theoretical Investigation Using DFT of 2,3-Diphenylquinoxaline Derivatives for Electronic and Photovoltaic Effects

Journal of Electronic Materials ◽

10.1007/s11664-021-09041-0 ◽

2021 ◽

Author(s):

Dorota Zając ◽

Dariusz Przybylski ◽

Jadwiga Sołoducho

Keyword(s):

Solar Cells ◽

Acrylic Acid ◽

Organic Semiconductors ◽

Organic Solar Cells ◽

Molecular Design ◽

Low Cost ◽

Design Synthesis ◽

Semiconducting Properties ◽

Homo Lumo

AbstractDeveloping effective and low‐cost organic semiconductors is an opportunity for the development of organic solar cells (OPV). Herein, we report the molecular design, synthesis and characterization of two molecules with D–A–D–A configuration: 2-cyano-3-(5-(8-(3,4-ethylenodioxythiophen-5-yl)-2,3-diphenylquinoxalin-5-yl)thiophen-2-yl)acrylic acid (6) and 2-cyano-3-(5-(2,3-diphenyl-8-(thiophen-2-yl)quinoxalin-5-yl)thiophen-2-yl)acrylic acid (7). Moreover, we investigated the structural, theoretical and optical properties. The distribution of HOMO/LUMO orbitals and the values of the ionization potential indicate good semiconducting properties of the compounds and that they can be a bipolar material. Also, the optical study show good absorption in visible light (λabs 380–550 nm). We investigate the theoretical optoelectronic properties of obtained compounds as potential materials for solar cells.

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