Azatriangulene-Based Conductive C═C Linked Covalent Organic Frameworks with Near-Infrared Emission.

Autor: Hamzehpoor E; Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 09B, Canada., Ghamari P; Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 09B, Canada., Tao Y; Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 09B, Canada., Rafique MG; Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 09B, Canada., Zhang Z; Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 09B, Canada., Salehi M; Department of Chemical Engineering, McGill University, 3610 University Street, Montreal, Quebec, H3A 0C5, Canada., Stein RS; Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 09B, Canada., Ramos-Sanchez J; Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 09B, Canada., Laramée AW; Département de chimie, Institut Courtois, Université de Montréal, 1375 Avenue Thérèse-Lavoie-Roux, Montréal, Québec, H2V 0B3, Canada., Cosa G; Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 09B, Canada., Pellerin C; Département de chimie, Institut Courtois, Université de Montréal, 1375 Avenue Thérèse-Lavoie-Roux, Montréal, Québec, H2V 0B3, Canada., Seifitokaldani A; Department of Chemical Engineering, McGill University, 3610 University Street, Montreal, Quebec, H3A 0C5, Canada., Khaliullin RZ; Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 09B, Canada., Perepichka DF; Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 09B, Canada.
Jazyk: angličtina
Zdroj: Advanced materials (Deerfield Beach, Fla.) [Adv Mater] 2024 Oct 21, pp. e2413629. Date of Electronic Publication: 2024 Oct 21.
DOI: 10.1002/adma.202413629
Abstrakt: Two near-infrared (NIR) emissive π-conjugated covalent organic frameworks (COFs) pTANG1 and pTANG2 are synthesized using Knoevenagel condensation of trioxaazatriangulenetricarbaldehyde (TATANG) with benzene- and biphenyldiacetonitriles, respectively. The morphology of the COFs is affected by the size of TATANG precursor crystals. Donor-acceptor interactions in these COFs result in small bandgaps (≈1.6 eV) and NIR emission (λ max = 789 nm for pTANG1). pTANG1 can absorb up to 9 molecules of water per unit cell, which is accompanied by a marked quenching of the NIR emission, suggesting applications as humidity sensors. p-Doping with magic blue significantly increases the electrical conductivities of the COFs by up to 8 orders of magnitude, with the room temperature conductivity of pTANG1 reaching 0.65 S cm -1 , the highest among reported C═C linked COFs. 1 H NMR relaxometry, temperature-dependent fluorescence spectroscopy, and DFT calculations reveal that the higher rigidity of the shorter phenylene linker is responsible for the more extended conjugation (red-shifted emission, higher electrical conductivity) of pTANG1 compared to pTANG2.
(© 2024 The Author(s). Advanced Materials published by Wiley‐VCH GmbH.)
Databáze: MEDLINE
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