Triptycene Derivative Polymer with Rotating Benzene Rings
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Solution Overview
Problem
Existing triptycene derivatives have a structure that hinders the rotation of benzene rings about the axis formed by barrelene, and their hydrophobic nature limits their applications in functional materials.
Innovation Solution
A polymerizable triptycene derivative with hydrophilic functional groups at positions 9 and/or 10, and (poly)ethylene glycol introduced between the polymerizable groups and the barrelene structure, allowing even rotation of benzene rings and enhancing compatibility with hydrophilic compounds.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Strength
If polymerizable groups are incorporated into the aromatic ring of the triptycene skeleton, then the compound can form polymer extension chains, but the rotation of benzene rings about the barrelene axis is hindered
Solution Approach 1:
The patent divides the molecular structure into distinct segments: the triptycene core skeleton and the polymerizable functional groups attached at positions 9 and 10. This segmentation allows the benzene rings to rotate freely about the barrelene axis while the polymerizable groups extend outward to form polymer chains, resolving the contradiction between maintaining rotational freedom and enabling polymerization.
Solution Approach 2:
The patent transitions from two-dimensional incorporation of polymerizable groups within the aromatic ring plane to three-dimensional attachment at the axial positions 9 and 10 of the triptycene skeleton. This dimensional change allows polymer chains to extend axially without interfering with the rotational freedom of the benzene rings in the equatorial plane.
2Stability of the object's composition
If triptycene derivatives with traditional structures are used, then the molecular structure is stable, but the hydrophobic nature limits applications in functional materials requiring hydrophilicity
Solution Approach 1:
The patent applies local quality modification by introducing hydrophilic polyethylene glycol groups at specific positions (9 and/or 10) of the triptycene skeleton while maintaining the hydrophobic aromatic core. This creates a amphiphilic molecule with distinct hydrophobic and hydrophilic regions, allowing the stable triptycene core to be preserved while gaining compatibility with hydrophilic compounds through the PEG side chains.
Solution Approach 2:
The patent creates a composite molecular structure combining the hydrophobic triptycene aromatic hydrocarbon core with hydrophilic polyethylene glycol side chains. This molecular composite achieves both structural stability from the rigid aromatic core and hydrophilicity from the PEG groups, enabling applications in both hydrophobic and hydrophilic environments.
3Stability of the object's composition
If unsaturated polymerizable functional groups are attached at positions 9 and 10, then rotation of benzene rings is less hindered, but the hydrophobic nature of alkenyl and alkynyl groups limits application versatility
Solution Approach 1:
The patent changes the chemical parameter of the polymerizable groups by replacing traditional hydrophobic alkenyl or alkynyl groups with polyethylene glycol-containing polymerizable groups. This parameter change maintains the polymerization capability and rotational freedom while adding hydrophilicity, thereby expanding the range of applicable functional materials.
Data Source
AI summary
It is an objective of the present invention to provide a novel polymerizable triptycene derivative and a polymer compound as constituent component thereof that has a structure in which three benzene rings arranged at the axis formed by barrelene of the triptycene skeleton can rotate evenly and that has hydrophilicity imparted to it as compared to any of the prior art triptycene derivatives and is thus highly useful in functional materials. The above objective is achieved by the polymerizable triptycene derivative and a polymer compound as constituent component thereof having substituents with an unsaturated bonding functional group at position 9 and/or position 10 of the triptycene skeleton, the polymerizable triptycene derivative having two carboxyl groups and the polymerizable triptycene derivative having one carboxyl group and one amino group.