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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.
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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.
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Optimized Crystal Framework by Asymmetric Core Isomerization in Selenium-Substituted Acceptor for Efficient Binary

Can Yang1, Qiaoshi An1, Mengyun Jiang1

  • 1Key Laboratory of Cluster Science of Ministry of Education, Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing, 100081, China.

Angewandte Chemie (International Ed. in English)
|October 12, 2023
PubMed
Summary

Researchers engineered novel selenium-containing small molecular acceptors (SMAs) for organic solar cells (OSCs). The optimized A-OSeF molecule achieved a record 18.5% power conversion efficiency in binary OSC devices.

Keywords:
Asymmetric AcceptorsCrystal EngineeringIsomerizationSeleniumSolar Cells

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Area of Science:

  • Materials Science
  • Organic Electronics
  • Photovoltaics

Background:

  • Small molecular acceptors (SMAs) are crucial for organic solar cell (OSC) efficiency.
  • Both structural isomerization and selenium substitution in SMAs impact device performance.
  • The synergistic effects of these modifications are not fully understood.

Purpose of the Study:

  • To investigate the combined effects of regional isomerization and selenium substitution in SMAs.
  • To develop novel SMAs with enhanced properties for efficient OSCs.
  • To establish structure-property relationships for selenium-containing SMAs.

Main Methods:

  • Synthesis of three isomeric SMAs (S-CSeF, A-ISeF, A-OSeF) with varied selenium positions and heteroaromatic rings.
  • Crystallographic analysis of A-OSeF to understand molecular packing.
  • Fabrication and characterization of OSC devices using the developed SMAs.
  • Analysis of film morphology, band gap, crystallinity, and charge mobility.

Main Results:

  • A-OSeF exhibited closer π-π stacking and more ordered 3D network packing.
  • Outward shift of selenium substitution led to wider band gaps, higher crystallinity, and improved electron mobility.
  • PM1:A-OSeF blend showed favorable fibrous morphology with ordered packing and efficient charge transport.
  • A-OSeF-based devices achieved a record 18.5% power conversion efficiency in binary OSCs.

Conclusions:

  • Precise molecular engineering of selenium position and heteroaromatic rings offers a synergistic approach.
  • Optimized molecular packing and charge transport are key to high-performance OSCs.
  • This work provides a promising strategy for developing top-ranked selenium-containing SMAs for OSC applications.