Halogenated Nanohoop Compounds for Uniform Columnar Assembly

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Solution Overview

Problem

Current carbon nanotube (CNT) synthesis methods face challenges such as insolubility, inhomogeneity, and ill-defined structure, limiting their uniformity and purity, and require complex chemical modifications for assembly, which hinders their full implementation in various applications.

Innovation Solution

Development of halogenated nanohoop compounds with halogen atoms coupled to their skeleton, allowing for easy assembly into uniform column-like structures through C—H/C—X interactions, forming networks via perhaloarene-arene non-covalent interactions, which can mimic CNT properties without the synthesis complexities.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional CNT synthesis methods are used, then CNTs can be produced with cylindrical channels and porous structure, but the resulting materials suffer from insolubility, inhomogeneity, and ill-defined structure

Engineering Contradiction:
Improvestructural uniformityVSAvoidsynthesis complexity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent divides the CNT structure into discrete nanohoop units with defined aromatic ring segments. Each nanohoop consists of a specific number of aromatic rings (e.g., [10]CPP with 10 rings) connected by single bonds, creating uniform, well-defined structural units that can be precisely controlled during synthesis, unlike the continuous and variable structure of conventional CNTs

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent changes the fundamental structural parameters from sp2-hybridized continuous carbon networks in CNTs to sp3-hybridized discrete nanohoops with defined bond angles and lengths. The nanohoops feature specific geometric parameters (e.g., 106° bond angles, 1.47 Å bond lengths) that enable uniform assembly and improve solubility while maintaining porous cylindrical channels

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If CNTs are used for molecular encapsulation and mass transport, then remarkable properties are achieved, but complex chemical modifications and coupling reactions are required for assembly

Engineering Contradiction:
Improvefunctional application rangeVSAvoidassembly process complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent implements self-assembly through non-covalent interactions between nanohoops. The molecules automatically organize into columnar assemblies and toroidal superstructures through π-π stacking and van der Waals forces, eliminating the need for complex chemical modifications or coupling reactions that would otherwise be required to achieve controlled assembly

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The patent creates composite hierarchical structures where individual nanohoops assemble into columns, which further organize into toroidal superstructures with central cavities. This multi-level composite organization provides versatile functionality for molecular encapsulation and mass transport while maintaining structural uniformity

Inventive Principle:
Principle #40Composite materials

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The halogenated nanohoop compounds and assemblies provide enhanced uniformity, purity, and modified porosity, enabling applications in energy storage, electronic devices, and biological transport, surpassing the limitations of conventional CNTs by facilitating host-guest chemistry and electronic conductivity.

Implementation Method 1

The nanohoop compounds can interact via C—H/C—X interactions (wherein X is a halogen atom selected from chloro, fluoro, bromo, or iodo) such that they assembly into a column-like structure (or an 'assembly' as described herein)

Methodology Applied
Scientific EffectC—H/C—X interaction: Van der Waals Force

Implementation Method 2

Assemblies described herein also can interact to form assembly networks, wherein perhaloarene-arene interactions act to non-covalently join the various assemblies into the network

Methodology Applied
Scientific EffectPerhaloarene-arene interaction: Van der Waals Force

Data Source

PatentUS10654780B2Halogenated nanohoop compounds and methods of making and using the same
Publication Date: 2020.05.19 UNIVERSITY OF OREGON
  • US10654780B2 patent drawing
  • US10654780B2 patent drawing
  • US10654780B2 patent drawing

AI summary

Disclosed herein are embodiments of halogenated nanohoop compounds and assemblies thereof that can be used to for a variety of biological and chemical applications. The halogenated nanohoop compounds described herein exhibit non-covalent interactions that promote their ability to stack and form column-like assemblies having uniform pore size and that do not exhibit structural defects typically associated with other column-like structures, such as carbon nanotubes. Assemblies described herein also are capable of non-covalent interactions with other assemblies and thus can be used to form networks of the assemblies described herein.