2D Poly(arylene vinylene) Covalent Organic Frameworks via Aldol Condensation of Trimethyltriazine

Designing structural order in electronically active organic solids remains a great challenge in the field of materials chemistry. Now, 2D poly(arylene vinylene)s prepared as highly crystalline covalent organic frameworks (COFs) by base‐catalyzed aldol condensation of trimethyltriazine with aromatic...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-09, Vol.58 (39), p.13753-13757
Main Authors: Jadhav, Thaksen, Fang, Yuan, Patterson, William, Liu, Cheng‐Hao, Hamzehpoor, Ehsan, Perepichka, Dmitrii F.
Format: Article
Language:English
Subjects:
2D materials
Aldehydes
aldol reaction
Condensation
Condensation polymerization
covalent organic frameworks
Organic chemistry
Organic solids
Polymers
Polyphenylene vinylene
Porosity
π-conjugation
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Summary:Designing structural order in electronically active organic solids remains a great challenge in the field of materials chemistry. Now, 2D poly(arylene vinylene)s prepared as highly crystalline covalent organic frameworks (COFs) by base‐catalyzed aldol condensation of trimethyltriazine with aromatic dialdehydes are reported. The synthesized polymers are highly emissive (quantum yield of up to 50 %), as commonly observed in their 1D analogues poly(phenylene vinylene)s. The inherent well‐defined porosity (surface area ca. 1000 m2 g−1, pore diameter ca. 11 Å for the terephthaldehyde derived COF‐1) and 2D structure of these COFs also present a new set of properties and are likely responsible for the emission color, which is sensitive to the environment. COF‐1 is highly hydrophilic and reveals a dramatic macroscopic structural reorganization that has not been previously observed in framework materials. Crystalline 2D poly(arylene vinylene) covalent organic frameworks (COFs) have been synthesized by base‐catalyzed aldol condensation of trimethyltriazine with a series of aromatic dialdehydes. The resulting COFs are hydrolytically stable and highly fluorescent (quantum yield ≤50 %). Addition of protic solvents results in a dramatic and reversible expansion of the bulk volume and red shifted emission of the COF.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201906976