Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2747 - 2755
Published: Jan. 1, 2024
A doubly helical boron-doped polycyclic aromatic hydrocarbon was synthesized, which showed a low LUMO level, high absorption coefficient and fluorescence ( Φ F = 0.73), combined with one-dimensional π–π stacking interaction in the solid state.
Language: Английский
Chemical Science, Journal Year: 2024, Volume and Issue: 15(20), P. 7408 - 7440
Published: Jan. 1, 2024
Recent advances in synthesis have opened the way to a variety of boron helicenes. We highlight main achievements these chiral compounds and discuss their photophysical properties potential as functional materials.
Language: Английский
Citations
18
JACS Au, Journal Year: 2025, Volume and Issue: 5(2), P. 756 - 765
Published: Jan. 23, 2025
Carbazolocarbazole (CCz) represents a novel class of heterocycles in the carbazole family, distinguished by its unique structure and related properties. However, significant challenges associated with synthesis have constrained exploration studies recent years. Herein, we presented thorough reproducible method for synthesizing gram-sized helical CCz, extending functionalization to investigate both pristine CCz six derivatives various substituents. This work is debut compounds displaying afterglow characteristics solid state. The demonstrated impressive ultralong room-temperature phosphorescence (URTP) lifetimes, ranging from 0.52 0.72 s, which are considered relatively long among family. URTP series occurs due efficient intersystem crossing (ISC) process singlet triplet-excited states, facilitated enhanced spin–orbit coupling (SOC). Based on comprehensive investigation seven compounds, proposed strategy elevating photoluminescence quantum yield (PLQY) organic emitters. Notably, most rigid derivatives, SpiroCCz, exhibited highest total PLQY 79.9%, one carbazole-based emitters polymer matrix. Overall, innovative promising candidates applications optoelectronic devices, bioimaging, security printing.
Language: Английский
Citations
1
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(43), P. 29782 - 29791
Published: Oct. 22, 2024
In this manuscript we present a strategy to achieve ultranarrowband circularly polarized luminescence (CPL) from multiple 1,4-azaborine-embedded helical nanographenes. The impact of number and position boron nitrogen atoms in the rigid core molecule on optical properties─including absorption emission maxima, photoluminescence quantum yield, Stokes shift, excited singlet–triplet energy gap full width at half-maximum (fwhm) for CPL fluorescence─was investigated. molecules reported here exhibits fluorescence (fwhm 16–17.5 nm toluene) 18–19 toluene). To best our knowledge, is among narrowest any organic date. Quantum chemical calculations, including computed spectra involving vibronic contributions, provide valuable insights future molecular design aimed achieving narrowband CPL.
Language: Английский
Citations
6
Chemical Science, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
Just four steps are required to transform 2-nitrobenzaldehyde into centrosymmetric, quadrupolar N,B-doped nanographenes possessing two nitrogen-boron dative bonds. A convergent fragment coupling strategy allowed rapid access key intermediates bearing...
Language: Английский
Citations
0
Journal of Luminescence, Journal Year: 2025, Volume and Issue: unknown, P. 121250 - 121250
Published: April 1, 2025
Language: Английский
Citations
0
Dyes and Pigments, Journal Year: 2025, Volume and Issue: 240, P. 112861 - 112861
Published: April 28, 2025
Language: Английский
Citations
0
Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown
Published: Aug. 19, 2024
Abstract Boron‐doped helicenes, known for their unique electronic and photophysical properties, are of great interest numerous applications. This research introduces two new azabora[6]helicenes, H[6]BN1 H[6]BN2 , synthesized through an efficient method. These molecules have boron nitrogen atoms in opposing positions, enhancing distinctive attributes. Both helicenes show excellent emission with exhibiting narrowband blue fluorescence circularly polarized luminescence (CPL), achieving g lum values 4~5×10 −4 which is beneficial chiroptical The addition a donor group, 3, 6‐di‐tert‐butyl‐9H‐carbazole, improves luminescence, likely due to enhanced molecular orbital overlap electron delocalization. ′s needle‐like single crystals exhibit mechanochromism, changing luminescent color from yellow green under mechanical stress, promising stimulus‐responsive materials. In conclusion, this study presents novel class BN[6]helicenes superior properties. Their combination features mechanochromism makes them ideal advanced materials, expanding the potential helicene‐based compounds offering directions synthesis specific characteristics.
Language: Английский
Citations
3
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 6, 2024
The semiconductor properties of nanosized graphene fragments, known as molecular nanographenes, position them exceptional candidates for next-generation optoelectronics. In addition to their remarkable optical and electronic features, chiral nanographenes exhibit high dissymmetry factors in circular dichroism circularly polarized luminescence measurements. However, the synthesis enantiomerically pure remains a significant challenge. Typically, these materials are synthesized racemic form, followed by separation enantiomers using high-performance liquid chromatography (HPLC). While effective, this method often requires expensive instrumentation, extensive optimization conditions, typically yields analytical quantities desired samples. An alternative approach is enantioselective nanographenes; however, date, only two examples have been documented literature. work, we present straightforward chemical resolution helical bilayer nanographenes. This enables effective scalable preparation while avoiding need HPLC. incorporation BINOL core into polyarene precursor facilitates diastereomers through esterification with camphorsulfonyl chloride. Following standard chromatographic column, hydrolysis group nanographene precursors. subsequent graphitization, achieved Scholl reaction, occurs an enantiospecific manner concomitant formation furan ring heterohelicene moiety. absolute configurations final enantiomers, P-oxa[9]HBNG M-oxa[9]HBNG, determined X-ray diffraction. Additionally, electrochemical, photophysical, chiroptical thoroughly evaluated.
Language: Английский
Citations
3
Chemical Science, Journal Year: 2024, Volume and Issue: 15(32), P. 12819 - 12826
Published: Jan. 1, 2024
Helicenes, featuring unique helical structures, have a long history as three-dimensional polycyclic aromatic hydrocarbons (PAHs). Incorporation of heteroatoms into helicenes may alter their electronic structures and achieve unexpected physical properties. Here, we disclose fusion boron-doped π-systems onto an efficient strategy to design carbohelicenes. Two double [6]carbohelicenes were synthesized, which possess the C58B2 C86B2 π-skeletons containing two [6]helicene subunits, respectively. The molecule thus represents largest-size helicene-based PAH. A thorough investigation reveals that helicene moieties boron atoms endow with delocalized well-tunable ground-state excited-state photophysical It is notable displays stimulated emission behavior amplified spontaneous (ASE) properties in not only blend films various doped concentrations but also pure film. To our knowledge, it first example ASE-active [n]helicene (n ≥ 6), moreover, such robust ASE performance has rarely been observed PAHs, demonstrating promising utility carbohelicenes for laser materials.
Language: Английский
Citations
2
Chemical Communications, Journal Year: 2024, Volume and Issue: 60(63), P. 8292 - 8295
Published: Jan. 1, 2024
Novel carbonyl-N embedded hetero[7]helicene diastereomers incorporating axially chiral binaphthyl were facilely synthesized and separated. The separated homochiral hetero[7]helicenes exhibit intense green photoluminescence circularly polarized luminescence (CPL) with dissymmetry factors (
Language: Английский
Citations
1