Pi-OF Framework Conductivity via Pi-Pi Interactions

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Solution Overview

Problem

Integration of organic frameworks into organic electronics, such as OFETs, OLEDs, and solar cells, is challenging due to poor electrical conductivity and solubility issues stemming from coordination, covalent, and hydrogen bonds.

Innovation Solution

A pi-pi interaction-constructed organic framework (pi-OF) with spirobifluorene units and 3-(dicyanomethylidene)indan-1-one units, which form a rigid biplanar cruciform shape, enabling pi-pi interactions and CH interactions for enhanced conductivity and stability, and can be used in conjunction with bioactive agents for controlled release.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If organic frameworks are integrated into organic electronics using coordination, covalent, and hydrogen bonds, then structural stability is improved, but electrical conductivity and solubility deteriorate

Engineering Contradiction:
Improvestructural stabilityVSAvoidelectrical conductivity
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent employs a composite material strategy by combining spirobifluorene units with 3-(dicyanomethylidene)indan-1-one units to create a hybrid organic framework. This composite structure integrates the structural stability of spirobifluorene with the electron-accepting and conductivity-enhancing properties of the dicyanomethylideneindan-1-one units, achieving both stability and improved electrical conductivity through material composition rather than traditional bonding approaches.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent applies local quality by creating regions with different functional properties within the framework. The spirobifluorene units provide structural rigidity and stability in certain regions, while the 3-(dicyanomethylidene)indan-1-one units contribute electron-accepting capabilities and conductivity in other regions. This spatial differentiation of functional properties allows the material to simultaneously achieve structural integrity and electrical conductivity without compromising either property throughout the entire structure.

Inventive Principle:
Principle #3Local quality

2Stability of the object's composition

If traditional organic frameworks use coordination, covalent, and hydrogen bonds, then framework stability is improved, but solubility deteriorates

Engineering Contradiction:
Improveframework stabilityVSAvoidsolubility
Core Design Contradiction:
Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

The patent utilizes parameter changes by modifying the chemical structure parameters of the framework units. The introduction of 3-(dicyanomethylidene)indan-1-one units with specific electronic and steric parameters alters the overall solubility characteristics of the framework while maintaining structural stability. This parameter modification approach enables the framework to achieve both stability and improved solubility by changing molecular-level parameters rather than altering the fundamental bonding architecture.

Inventive Principle:
Principle #35Parameter changes

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 pi-OF framework provides improved electrical conductivity and thermal stability, enabling applications in organic electronics and drug delivery systems, with the ability to self-assemble into porous structures for efficient charge transport and bioactive agent release.

Implementation Method 1

Each IC unit is configured to interact via a pi-pi interaction with a neighboring IC unit of an adjacent molecular structure

Methodology Applied
Scientific EffectPi-pi interaction: London Dispersion Force

Implementation Method 2

interact via a CH-interaction with neighboring aromatic group (R1) of an adjacent molecular structure

Methodology Applied
Scientific EffectCH-interaction: Van der Waals Force

Implementation Method 3

illuminating the composition after the injecting with light to cause at least a portion of the bioactive agent to be released in response to the illuminating

Methodology Applied
Scientific EffectPhoto-induced release: Photodissociation

Data Source

PatentUS20240308972A1Non-Covalent Pi-Pi Interaction Constructed Organic Frameworks (PiOFs)
Publication Date: 2024.09.19 RGT UNIV OF CALIFORNIA
  • US20240308972A1 patent drawing
  • US20240308972A1 patent drawing
  • US20240308972A1 patent drawing

AI summary

A composition having a pi-pi interaction-constructed organic framework (p-OF). The pi-OF includes a plurality of molecular structures, each molecular structure, including: (a) a centroid core having two spirobifluorene (SF) units, the two SF units forming a rigid biplanar conjugated cruciform-shaped spirobifluorene. the two SF units forming an essentially orthogonal configuration; and (b) a plurality of multijoint fragment units, each unit comprising a 3-dicyanomethylidene)indan-1-one (IC) unit, each IC unit is used as an end group (EG) to each end of the two spirobifluorene (SF) units. Each IC unit is configured to interact via a pi-pi interaction with a neighboring IC unit of an adjacent molecular structure or to interact via a CH-interaction with neighboring aromatic group (R1) of an adjacent molecular structure, or both. The composition also includes a bioactive agent absorbed into the pi-OF.