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Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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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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Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...

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Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

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Self-assembled tetragonal prismatic molecular cage highly selective for anionic π guests.

Cristina García-Simón¹, Marc Garcia-Borràs, Laura Gómez

¹QBIS Group, Departament de Química, Institut de Química Computacional I Catàlisis (IQCC), Universitat de Girona, Campus Montilivi, E17071 Girona, Catalonia, Spain.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|December 6, 2012

Summary

Researchers developed a new nanocapsule for host-guest chemistry. This supramolecular nanovessel selectively binds anionic guests and can tune properties of metal complexes, showing promise for sensors and nanoreactors.

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Published on: March 24, 2018

Area of Science:

Supramolecular Chemistry
Nanotechnology
Materials Science

Background:

Metal-directed supramolecular synthesis enables the creation of functional nanosized molecules.
Porphyrin-based hosts exhibit strong affinity for guest molecules, making them suitable for host-guest chemistry.

Purpose of the Study:

To synthesize and characterize a novel nanocapsule with a tetragonal prismatic geometry.
To investigate the host-guest chemistry and molecular recognition capabilities of the new nanocapsule.
To explore the potential applications of the nanocapsule in hosting and modifying metal complexes.

Main Methods:

Supramolecular synthesis of the nanocapsule 3·(CF(3)SO(3))(8) using dipalladium hexaazamacrocyclic complex (Pd-1) and a tetraanionic porphyrin derivative.
Characterization using Nuclear Magnetic Resonance (NMR), UV/Vis spectroscopy, Electrospray Ionization Mass Spectrometry (ESI-MS), and Diffusion Ordered Spectroscopy (DOSY).
Density Functional Theory (DFT) calculations to understand guest-host interactions.

Main Results:

The nanocapsule exhibits a tetragonal prismatic A(4 B(2) geometry.
Highly selective molecular recognition was observed for anionic, planar-shaped π guests, with association constants exceeding 10(9) M(-1).
The nanocapsule can host single molecules of M(dithiolene)(2) complexes (M=Au, Pt, Pd, Ni) and tune their optical and redox properties.

Conclusions:

The synthesized nanocapsule is a promising candidate for host-guest chemistry due to its selective binding of anionic guests.
The ability to tune the properties of encapsulated metal complexes opens avenues for applications in sensing and nanoreactors.
The straightforward synthesis of the nanocapsule and its building blocks facilitates the development of polyfunctional supramolecular nanovessels.