Design and Synthesis of Fluorescent 1,3-Diaryl-β-carbolines and 1,3-Diaryl-3,4-dihydro-β-carbolines

Abstract

The 1,3-diaryl-β-carboline derivatives, including 3,4-dihydro variants, were synthesized via a multiple-step approach. These compounds possess rigid and twisted configurations, which are expected to exhibit unique optical properties. The absorption and fluorescence properties of the newly synthesized compounds were investigated. These synthetic 1,3-diaryl-β-carbolines displayed strong emission in the range of 387–409 nm and exhibited absolute photoluminescence quantum yields of up to 74%. Density functional theory calculations were performed to better elucidate the geometric, electronic, and optical properties of these novel 1,3-diaryl-β-carbolines.

Construction of High-Performance Carbene–Metal–Amide-Like TADF Materials: A Theoretical Study

“…Heteroatom modification of carbazole-based materials represents one of the most efficient approaches to endow materials with unique physical and chemical properties. − For instance, α-carboline and β-carboline work well in terms of good quantum efficiency in OLEDs due to their efficient electron-donating properties and high singlet/triplet energy levels. , Herein, on the basis of CMA1, we designed four molecules by regulating the location (α, β) and number of N atoms to theoretically design CMA-based TADF molecules and elucidate their structure–property relationships (Figure ). It was found that the materials with the replacement of carbazole by α-carboline and β-carboline could maintain the favorable TADF properties with both small splitting energy and large fluorescence oscillator strength.…”

Electron rich substituted β-carboline derivatives: Synthesis and photophysical properties

“…[15] Reports on the photophysical properties of more substituted β-carbolines are rather scarce in the literature. [15][16][17][21][22][23][24][25][26][27][28][29][30] Given the lack of studies of β-carboline absorption and fluorescence, we propose in the present work to explore the impact of the substitution at position 1 on the spectral properties of neutral and protonated β-carboline derivatives. In more details, the substitution by two electron donating groups (methoxy and dimethylamino), one accepting moiety (trifluoromethyl), connected through three different spacers (aryl, styryl and ethynyl) are investigated.…”

Synthesis of Tryptamines from Radical Cyclization of 2-Iodoaryl Allenyl Amines and Coupling with 2-Azallyls

“…We note that in 2021 Wu, Zhang, Chruma, and co-workers also reported the synthesis of tryptamine derivatives using 2-azaallyl anion nucleophiles. 46 This work is complementary to the method described herein, with reactions proceeding largely through two-electron processes performed on indole core structures (Scheme 1e). 46…”

“…46 This work is complementary to the method described herein, with reactions proceeding largely through two-electron processes performed on indole core structures (Scheme 1e). 46…”