Citation: SHU Jie, TANG Dan-Dan, WANG Ning. Investigation of Structure of Perylene Diimides Based Materials by Using Advanced Solid State Nuclear Magnetic Resonance Techniques:A Study on Molecular Assembly, Interfacial Interaction and Miscibility[J]. Chinese Journal of Analytical Chemistry, ;2019, 47(8): 1170-1179. doi: 10.19756/j.issn.0253-3820.191107 shu

Investigation of Structure of Perylene Diimides Based Materials by Using Advanced Solid State Nuclear Magnetic Resonance Techniques:A Study on Molecular Assembly, Interfacial Interaction and Miscibility

Analysis and Testing Center, Soochow University, Suzhou 215123, China

Received Date: 25 February 2019
Revised Date: 16 June 2019

Fund Project: This work was supported by the National Natural Science Foundation of China (Nos. 21673148, 21303111).

In recent years, perylene diimide (PDI) derivatives have attracted enormous attentions owing to their favorable properties as the alternative electron acceptor to PCBM in bulk heterojunction (BHJ) materials. It has been noted that the molecular local arrangement largely affects the performance of the BHJ devices. In this work, two PDI derivatives (named PDI and PDI) and their blends with poly(3-hexylthiophene)(P3HT) were investigated by using advanced solid state nuclear magnetic resonance(SSNMR). The ¹H-¹H SQ-DQ spectra revealed that both PDI and PDI molecules had ordered arrangement through π-π interaction. PDI showed higher molecular ordering than PDI. The blends of PDI and P3HT(PDI:P3HT) as well as PDI and P3HT(PDI:P3HT) were also investigated. Based on the features of ¹³C-¹H frequency switched Lee-Goldburg heteronuclear dipolar-correlation spectroscopy (FSLG-HETOCR) spectra, we revealed the phase-segregated structures for both PDI:P3HT and PDI:P3HT. Moreover, PDI exhibited reduced local ordering when blended with P3HT. Whilst PDI demonstrated different molecular local assembling structure. By fitting the BaBa DQ sideband pattern, the inter-nuclear distance of two neighboring PDI molecules was calculated. The interfacial information of PDI:P3HT was also obtained from 1D ¹³C{¹H} CP and ¹³C-¹H FSLG-HETOCR spectra. Based on the ¹³C chemical shifts and ¹³C-¹H correlation peaks, we suggested that in the interfacial area the PDI imide alkyl units located in the shielding zone of P3HT thiophene rings. The quantitative local mobility study was conducted through analyzing the rotor-encoded rotational echo double resonance (REREDOR) data. The deduced heteronuclear coupling constants via fitting the sideband patterns showed identical trend as the findings from the structural characterization. In addition to the structural investigation, this work suggested a possible characterizing strategy by using SSNMR techniques for the PDI based materials or other conjugated systems.
- Perylene diimide,
- Solid state nuclear magnetic resonace,
- Assembling structure,
- Miscibility,
- Poly(3-hexylthiophene)
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