N1,N1-Bis(4-aminophenyl)benzene-1,4-diamine trihydrochloride
CAS Number:
114254-48-7
Molecular Formula:
C18H21Cl3N4
Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes
Literature Information
Publication Date
2023-12-04
DOI
10.1039/D3QO01914D
Impact Factor
5.281
Authors
Krzysztof Bartkowski, Abhishek Kumar Gupta, Tomas Matulaitis, Maja Morawiak, Eli Zysman-Colman, Marcin Lindner
View Original
Abstract
We report the synthesis and characterization of the first pyrrolizine-embedded PAH systems. The bipolar core, based on a naphthalimide and indole fusion, was successfully synthesized through a one-pot cascade of Suzuki/Boc deprotection/Buchwald–Hartwig transformations. A facile post-functionalization of the unoccupied β-position of the heterocycle with aromatic amines as donor subunits led to a set of donor–acceptor architecture-based dyes. Effective narrowing of the HOMO–LUMO gap, along with its tuning by changing donor strength together with stabilization of π conjugation within the pyrrolizine–NMI core, provided a route to near-infrared (NIR) emission not only in solution (∼740 nm) but also in the solid-state (∼700 nm).
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
(S)-(9H-Fluoren-9-yl)methyl (pyrrolidin-2-ylmethyl)carbamate hydrochloride
CAS Number:
1217813-15-4
Molecular Formula:
C20H23ClN2O2
![[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid structure](https://static.chemtradehub.com/structs/509/50918-26-8-4ce8.webp "[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid structure")
[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid
CAS Number:
50918-26-8
Molecular Formula:
C5H6N2O2S2
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