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Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
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Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Bis- and mono(m-benzoic acid)-functionalized pillar[5]arenes.

Xin-Lang Wu1, Yi Chen, Wen-Jing Hu

  • 1Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 20044, P.R. China.

Organic & Biomolecular Chemistry
|May 26, 2017
PubMed
Summary

Functionalizing pillar[5]arenes with m-benzoic acid created new molecules. These compounds self-assembled into channels or formed bicyclic structures, with one forming a self-included complex.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Pillar[5]arenes are macrocyclic hosts with tunable cavities.
  • Functionalization of macrocycles is key to designing novel self-assembled structures.

Purpose of the Study:

  • To synthesize and characterize novel m-benzoic acid-functionalized pillar[5]arenes.
  • To investigate the self-assembly behavior and complexation properties of these functionalized macrocycles.

Main Methods:

  • Synthesis of bis- and mono(m-benzoic acid)-functionalized pillar[5]arenes.
  • X-ray crystallography to determine structures of self-assembled products.
  • Spectroscopic analysis to confirm functionalization and complexation.

Main Results:

  • Bis(m-benzoic acid)-functionalized pillar[5]arene self-assembled into 1D channels encapsulating DMF.
  • Esterification of the bis-functionalized pillar[5]arene with decane-1,10-diol yielded a bicyclic compound, not a catenane.
  • Mono(m-benzoic acid)-functionalized pillar[5]arene derivatives showed self-inclusion complex formation.

Conclusions:

  • M-benzoic acid functionalization provides a route to diverse pillar[5]arene architectures.
  • Pillar[5]arene cavity size and functional group placement influence self-assembly and complexation outcomes.
  • The study demonstrates the potential of functionalized pillar[5]arenes in creating complex supramolecular structures.