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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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A Structurally Variable Porous Organic Salt Based on a Multidirectional Supramolecular Cluster.

Tetsuya Miyano1, Naoki Okada1, Ryunosuke Nishida1

  • 1Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka, 565-0871, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 9, 2016
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A novel porous organic salt (POS) forms five crystal types by recognizing guest molecule differences. This adaptable material shows potential for highly sensitive chemical sensors.

Keywords:
cluster compoundscrystal engineeringfluorescencehost-guest systemssupramolecular chemistry

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Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Crystallography

Background:

  • Porous organic salts (POS) are crystalline materials with tunable structures.
  • Designing POS with variable porous networks remains a challenge.
  • Guest molecule recognition is crucial for developing advanced chemical sensors.

Purpose of the Study:

  • To design and synthesize a structurally variable porous organic salt (POS).
  • To investigate the formation of different POS crystal structures based on guest molecules.
  • To explore the potential of the developed POS for chemical sensing applications.

Main Methods:

  • Hierarchical design of a POS based on supramolecular clusters.
  • Synthesis of POS using 2-sulfophenyl anthracene (2-SPA) and triphenylmetylamine (TPMA).
  • X-ray crystallographic analysis to determine crystal structures and conformers.
  • Fluorescence spectroscopy to analyze guest molecule interactions.

Main Results:

  • Formation of five types of porous crystals (POS-a-e) by the POS material.
  • Identification of six conformers of the organic salt due to phenylene group motion.
  • Correlation between POS crystal structure, conformers, and guest molecule properties.
  • POS crystals exhibited fluorescence spectra sensitive to guest molecule structural and electronic variations.

Conclusions:

  • A structurally variable POS was successfully designed and synthesized.
  • The POS material demonstrates hierarchical self-assembly into diverse porous networks.
  • The observed fluorescence response suggests potential for sensitive chemical sensing.