An Efficient Ultrasound‐Assisted Synthesis of <i>N</i>‐Alkyl Derivatives of Carbazole, Indole, and Phenothiazine

Zhao, Sanhu; Kang, Jin Soo; Du, Yuting; Kang, Jingyan; Zhao, Xiaoni; Xu, Yinfeng; Chen, Ruixi; Wang, Qianqian; Shi, Xitao

doi:10.1002/jhet.1652

Cited by 22 publications

(13 citation statements)

References 29 publications

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“…Additionally, the method herein employed does not require direct handling of an alkyl halide or dimethyl sulfate, therefore eliminating the respective health risks. We demonstrate that quaternary ammonium salts allow for feasible and simple alkylation reactions in organic synthesis [13,14].…”

Section: Resultsmentioning

confidence: 95%

A Novel and Chemoselective Process ofN-Alkylation of Aromatic Nitrogen Compounds Using Quaternary Ammonium Salts as Starting Material

González-González

Vega

Monroy

et al. 2017

Journal of Chemistry

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The process of N-alkylation of several pyrroles, indoles, and derivative heterocycles is herein described, using quaternary ammonium salts as the source of an alkylating agent. These reactions were carried out on several heterocyclic rings with triethylbenzylammonium chloride or tetradecyltrimethylammonium bromide and an NaOH solution at 50%, leading to a chemoselective N-alkylated product and an average yield of 73%. This is an alternative process to the traditional benzylation and methylation of N-heterocycles with direct handling of alkyl halides.

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Section: Resultsmentioning

confidence: 95%

A Novel and Chemoselective Process ofN-Alkylation of Aromatic Nitrogen Compounds Using Quaternary Ammonium Salts as Starting Material

González-González

Vega

Monroy

et al. 2017

Journal of Chemistry

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“…Step 1: The synthesis of 9‐propagylcarbazole. [ 46,47 ] 1.26 g KOH solid was added into 30 mL carbazole solution (2.5 g carbazole dissolved in 30 mL dimethylformamide) at 0 °C. The solution was stirred at 0 °C for 20 min.…”

Section: Methodsmentioning

confidence: 99%

Photophysics and Spin‐Physics Studies on Persistent Upconversion Luminescence from Nonlinearly Polarizable Ferroelectric‐Like Lattice Prepared by Orderly Packing Donor–Acceptor Structures under Multiphoton Excitation

Dou

Demangeat

Wang

et al. 2022

Advanced Optical Materials

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The ultralong‐lived upconversion luminescence with the lifetime of 0.48 s in a broad spectral range (530–650 nm) is observed in CD49 (9‐(3‐(5‐bromopyridin‐3‐yl)prop‐2‐yn‐1‐yl)‐9H‐carbazole) crystal designed with donor–acceptor (carbazole–pyridine) structures under infrared excitation, simultaneously accompanied with second harmonic generation (SHG). This phenomenon indicates orderly packing donor–acceptor structures form a nonlinearly polarizable ferroelectric‐like lattice with ultralong‐lived light‐emitting states, leading to much prolonged nonlinear optical behaviors. The persistent upconversion luminescence together with SHG is largely reduced when lowering crystallinity. This implies that nonlinearly polarizable ferroelectric‐like lattice provides the necessary condition to generate persistent upconversion luminescence. Evidently, persistent upconversion luminescence becomes completely lacking when only using ultralong‐lived light‐emitting states without nonlinearly polarizable ferroelectric‐like lattice, exampled by 4‐(dimethylamino)benzonitrile dispersed in polyvinyl alcohol matrix. Magneto‐photoluminescence shows that persistent upconversion luminescence is essentially a super‐delayed fluorescence from crystalline intermolecular charge‐transfer excitons formed in the nonlinearly polarizable ferroelectric‐like lattice. Magnetodielectrics indicate crystalline intermolecular charge‐transfer excitons are coupled with nonlinearly polarizable ferroelectric‐like lattice, leading to prolonged nonlinear optical behaviors shown as persistent upconversion luminescence through super delayed fluorescence. Therefore, crystalline intermolecular charge‐transfer excitons formed in nonlinearly polarizable ferroelectric‐like lattice provide an interesting platform to generate prolonged nonlinear optical behaviors toward developing persistent upconversion luminescence under multiphoton excitation.

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“…9-H-propargylcarbazole. Synthesis was adapted from the literature 51,52 . Solid KOH (1.26 g, 22.5 mmol) was added to a solution of carbazole (2.5 g, 15.0 mmol) in DMF (30 mL) at 0°C.…”

Section: Methodsmentioning

confidence: 99%

Spin-orbital coupling and slow phonon effects enabled persistent photoluminescence in organic crystal under isomer doping

et al. 2021

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When periodically packing the intramolecular donor-acceptor structures to form ferroelectric-like lattice identified by second harmonic generation, our CD49 molecular crystal shows long-wavelength persistent photoluminescence peaked at 542 nm with the lifetime of 0.43 s, in addition to the short-wavelength prompt photoluminescence peaked at 363 nm with the lifetime of 0.45 ns. Interestingly, the long-wavelength persistent photoluminescence demonstrates magnetic field effects, showing as crystalline intermolecular charge-transfer excitons with singlet spin characteristics formed within ferroelectric-like lattice based on internal minority/majority carrier-balancing mechanism activated by isomer doping effects towards increasing electron-hole pairing probability. Our photoinduced Raman spectroscopy reveals the unusual slow relaxation of photoexcited lattice vibrations, indicating slow phonon effects occurring in ferroelectric-like lattice. Here, we show that crystalline intermolecular charge-transfer excitons are interacted with ferroelectric-like lattice, leading to exciton-lattice coupling within periodically packed intramolecular donor-acceptor structures to evolve ultralong-lived crystalline light-emitting states through slow phonon effects in ferroelectric light-emitting organic crystal.

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An Efficient Ultrasound‐Assisted Synthesis of N‐Alkyl Derivatives of Carbazole, Indole, and Phenothiazine

Cited by 22 publications

References 29 publications

A Novel and Chemoselective Process ofN-Alkylation of Aromatic Nitrogen Compounds Using Quaternary Ammonium Salts as Starting Material

A Novel and Chemoselective Process ofN-Alkylation of Aromatic Nitrogen Compounds Using Quaternary Ammonium Salts as Starting Material

Photophysics and Spin‐Physics Studies on Persistent Upconversion Luminescence from Nonlinearly Polarizable Ferroelectric‐Like Lattice Prepared by Orderly Packing Donor–Acceptor Structures under Multiphoton Excitation

Spin-orbital coupling and slow phonon effects enabled persistent photoluminescence in organic crystal under isomer doping

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