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- W3129166180 abstract "Abstract The naphthalenediimide (NDI) scaffold in contrast to its higher congeners possess low‐fluorescence. In spite of elegant synthetic developments, a highly emissive NDI is quite rare to find, as well as, a green‐light‐emitting NDI is yet to be explored. Herein, we report a novel class of symmetric and asymmetric NH 2 ‐substituted core‐NDIs ( 1 – 5 ) with tunable fluorescence in the visible region and extending to the NIR frontier. Importantly, the bis‐NH 2 ‐substituted NDI 2 revealed quantum yield, of ≈81 and ≈68 % in toluene and DMSO, respectively, suggesting versatility of the fluorophore in a wide range of solvent polarity. The dye 1 is shown to be the first NDI‐based green‐light emitter. The donor piperidine group in 5 diminish the by 40‐fold providing a lever to modulate the excited‐state intramolecular proton transfer (ESIPT) process. Our synthetic protocol applies a Pd catalyst and a benign hydride source simplifying the non‐trivial −NH 2 group integration at the NDI‐core. TD‐DFT calculations predicted strong intramolecular hydrogen bonds in the excited state in the bulk nonpolar medium and responsiveness to solvent polarity. The maximization of the NDI emission outlined here would further boost the burgeoning repertoire of applications of the NDI scaffold." @default.
- W3129166180 created "2021-02-15" @default.
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- W3129166180 creator A5089215837 @default.
- W3129166180 date "2021-03-16" @default.
- W3129166180 modified "2023-09-30" @default.
- W3129166180 title "Naphthalenediimides with High Fluorescence Quantum Yield: Bright‐Red, Stable, and Responsive Fluorescent Dyes" @default.
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- W3129166180 doi "https://doi.org/10.1002/chem.202100020" @default.
- W3129166180 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/33539577" @default.
- W3129166180 hasPublicationYear "2021" @default.
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