Related Experiment Video

Updated: Apr 15, 2026

Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups

Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups

Published on: February 11, 2012

Synthesis, Structure, and Air-stable N-type Field-Effect Transistor Behaviors of Functionalized

Chengyuan Wang¹, Jing Zhang¹, Guankui Long¹

¹School of Materials Science and Engineering, Nanyang Technological University Singapore, 639798 Singapore (Singapore).

Angewandte Chemie (International Ed. in English)

|April 2, 2015

Abstract:

Increasing the length of N-heteroacenes or their analogues is highly desirable because such materials could have great potential applications in organic electronics. In this report, the large π-conjugated N-heteroquinone 6,10,17,21-tetra-((triisopropylsilyl)ethynyl)-5,7,9,11,16,18,20,22-octaazanonacene-8,19-dione (OANQ) has been synthesized and characterized. The as-prepared OANQ shows high stability under ambient conditions and has a particularly low LUMO level, which leads to it being a promising candidate for air-stable n-type field-effect transistors (FETs). In fact, FET devices based on OANQ single crystals have been fabricated and an electron mobility of up to 0.2 cm(2) V(-1) s(-1) under ambient conditions is reported. More importantly, no obvious degradation was observed even after one month. Theoretical calculations based on the single crystal are consistent with the measured mobility.

Keywords:

X-ray diffraction conjugation density functional calculations electron transport heterocycles

More Related Videos

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry

Published on: March 4, 2021

Related Concept Videos

Structure of Conjugated Dienes

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the...

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

Structures of Carboxylic Acid Derivatives

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...

Exceptions to the Octet Rule

Exceptions to the Octet Rule

Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:

Nomenclature of Alkynes

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:

Articles linked to this work by shared authors, journal, and citation graph.

Flexible Linker Engineering of Dimeric Acceptors Enables Synergistic Modulation of Dielectric Constant and Spatial Conjugation for Organic Solar Cells Exceeding 20% Efficiency.

Angewandte Chemie (International ed. in English)·2026

HSAB-Guided Design of Chiral Osmium Halides With Both Efficient Nonlinear Optical Properties and High Stability.

Angewandte Chemie (International ed. in English)·2026

Linker-Mediated Trade-Off Between Acceptor Aggregation and Donor-Acceptor Mixing Enables Organic Solar Cells With Efficiencies Exceeding 20.5.

Angewandte Chemie (International ed. in English)·2026

Microbiome and aging: Trajectories of microbiome age across human ecosystems and their systemic effects.

iMeta·2026

Electrostatic Modulation of Central Units Enables High-Performance Fused-Ring Trimeric Acceptors.

Angewandte Chemie (International ed. in English)·2026

Chiral Quantum-Cutting.

Journal of the American Chemical Society·2026

See all related articles