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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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A dithieno[3,2-b:2',3'-d]pyrrole based, NIR absorbing, solution processable, small molecule donor for efficient bulk

Manohar Reddy Busireddy1, Venkata Niladri Raju Mantena1, Narendra Reddy Chereddy1

  • 1Crop Protection Chemicals Division, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India. chereddynarendra@gmail.com jrao@iict.res.in.

Physical Chemistry Chemical Physics : PCCP
|November 17, 2016
PubMed
Summary

A new organic small molecule donor, ICT3, was synthesized for organic solar cells. Annealing the active layer significantly boosted power conversion efficiency to 6.53%, demonstrating its potential for efficient energy conversion.

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Printing Fabrication of Bulk Heterojunction Solar Cells and In Situ Morphology Characterization
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Area of Science:

  • Materials Science
  • Organic Electronics
  • Photovoltaics

Background:

  • Organic small molecular donors are crucial for efficient bulk heterojunction solar cells (BHJSCs).
  • Developing novel materials with improved thermal stability, solubility, and optoelectronic properties is essential for advancing BHJSC technology.

Purpose of the Study:

  • To synthesize and characterize a novel organic small molecular donor material, ICT3, with a dithieno[3,2-b:2',3'-d]pyrrole (DTP) donor moiety and butylrhodanine acceptor moiety.
  • To investigate the thermal, photophysical, electrochemical, and photovoltaic properties of ICT3.
  • To fabricate and optimize BHJSCs using ICT3 and evaluate their performance.

Main Methods:

  • Synthesis of ICT3 with an A-D-D-D-A architecture.
  • Thermal analysis (TGA), solubility tests, UV-Vis absorption spectroscopy, cyclic voltammetry.
  • Fabrication of BHJSCs with ICT3:PC71BM active layers.
  • Optimization of active layer morphology through thermal and solvent vapor annealing.
  • Characterization of active layer morphology using X-ray diffraction (XRD) and atomic force microscopy (AFM).

Main Results:

  • ICT3 exhibits excellent thermal stability (Td = 372 °C) and good solubility (30 mg mL-1).
  • ICT3 shows broad visible region absorption (520-820 nm) and suitable energy levels for efficient charge transfer with PC71BM.
  • BHJSCs fabricated with ICT3 achieved a power conversion efficiency (PCE) of 3.04% as-cast, which improved to 4.94% after thermal annealing and 6.53% after thermal and solvent vapor annealing.
  • Annealing treatments improved crystallinity and nanoscale morphology, leading to enhanced exciton dissociation, charge transport, and reduced recombination.

Conclusions:

  • The novel ICT3 small molecule donor demonstrates promising properties for BHJSCs.
  • Post-fabrication annealing is critical for optimizing the performance of ICT3-based BHJSCs.
  • The achieved PCE of 6.53% highlights the potential of DTP-based small molecules for efficient organic photovoltaics.