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Theoretical prediction of structures and inclusion properties of heteroatom-bridged pillar[n]arenes

  • Ju XieEmail author
  • Chao Shen
  • Huizhong Shi
  • Shasha Luo
  • Maoxia He
  • Ming ChenEmail author
Original Research
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Abstract

In this paper, the heteroatom-bridged pillar[n]arene derivatives, namely bora-, aza-, and oxa-pillar[n]arenes (PnX, X = B, N, and O respectively, n = 4 − 6) are studied by quantum chemical calculations at the ωB97XD/6-311G(d,p) level of theory. The geometries, energetics, electronic structures, absorption spectra, solvent effects, and the inclusion complexation with paraquat dication are discussed in detail. The calculated results show the structures of pentamers (P5X) are more stable compared with tetramers (P4X) and hexamers (P6X) and the PnB have relatively loose and irregular geometry structures. The molecular cavities of PnX are electron-rich and capable of accommodating cationic guests. Absorption spectra of PnN and PnO are very similar to those of Pn with one intense peak (λmax) at around 260 nm, while PnB indicates another characteristic peak between 300 and 400 nm. P5X can form inclusion complexes of 1:1 stoichiometry with paraquat dication, and P5N exhibits strongest combination ability with paraquat dication among them. These thorough understanding of the structure and properties of heteropillar[n]arenes will broaden the designs, syntheses, and applications of pillararenes.

Keywords

Heteroatom-bridged pillar[n]arene Structure and property Density functional theory calculation 

Notes

Funding information

This work was supported by Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD); Top-notch Academic Programs Project of Jiangsu Higher Education Institutions (TAPP, PPZY2015B112); 111 Project, B12015; Postgraduate Research & Practice Innovation Program of Jiangsu Province (XKYCX18_052), and Science and Technology Innovation Foundation of Chenxi Project for Students of Yangzhou University (CX2018086).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflicts of interest.

Supplementary material

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ESM 1 (DOC 2574 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.School of Chemistry and Chemical EngineeringYangzhou UniversityYangzhouChina
  2. 2.Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education)Nankai UniversityTianjinChina
  3. 3.Environment Research InstituteShandong UniversityQingdaoChina

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