Related Experiment Video
Updated: Mar 7, 2026
08:07
Ultrahigh Density Array of Vertically Aligned Small-molecular Organic Nanowires on Arbitrary Substrates
Published on: June 18, 2013
15.5K
Naphthobischalcogenadiazole Conjugated Polymers: Emerging Materials for Organic Electronics
1RIKEN Center for Emergent Matter Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
Advanced Materials (Deerfield Beach, Fla.)
|February 28, 2017
Summary
Naphthobischalcogenadiazoles (NXzs) are novel building blocks for π-conjugated polymers, enhancing organic electronics. Polymers utilizing these units show high performance in organic field-effect transistors and organic photovoltaics, with NTz-based polymers achieving over 10% efficiency.
Area of Science:
- Materials Science
- Organic Electronics
- Polymer Chemistry
Background:
- π-Conjugated polymers are crucial for organic electronics like organic field-effect transistors (OFETs) and organic photovoltaics (OPVs).
- Donor-acceptor polymers are widely used, with benzochalcogenadiazoles (BXzs) being common acceptor units.
- Developing new building units is key to advancing polymer performance.
Purpose of the Study:
- To summarize the synthesis, properties, and structures of naphthobischalcogenadiazoles (NXzs) and their derived polymers.
- To highlight the device performance of these novel π-conjugated polymers.
- To discuss the structure-property relationships governing their performance.
Main Methods:
- Synthesis of naphthobischalcogenadiazoles (NXzs), including naphthobisthiadiazole (NTz), naphthobisoxadiazole (NOz), and naphthobisselenadiazole (NSz).
- Characterization of the electronic properties and self-assembling nature of NXzs and their polymers.
- Fabrication and testing of organic electronic devices (OFETs and OPVs) using these polymers.
Main Results:
- NXzs exhibit unique electronic properties and strong self-assembly capabilities, beneficial for π-conjugated polymers.
- Polymers incorporating NXzs demonstrate excellent performance in OFETs and OPVs.
- NTz-based polymers achieved over 10% power conversion efficiency in OPVs, representing a significant advancement.
Conclusions:
- NXzs are promising building units for high-performance organic electronic materials.
- The structure-property relationships of NXz-based polymers are critical for optimizing device performance.
- Further research into NXzs can lead to next-generation organic electronic devices.
Related Concept Videos
01:26Photochemical Electrocyclic Reactions: Stereochemistry
2.3K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Selection Rules: Photochemical Activation
2.3K
01:26Thermal and Photochemical Electrocyclic Reactions: Overview
3.1K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
3.1K
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
3.7K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.7K
01:20Anionic Chain-Growth Polymerization: Overview
2.7K
The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
2.7K
01:17Ziegler–Natta Chain-Growth Polymerization: Overview
4.1K
Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
4.1K
01:17Thermal Electrocyclic Reactions: Stereochemistry
2.7K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.7K