Efficient manipulation of Förster resonance energy transfer through host–guest interaction enables tunable white-light emission and devices in heterotopic bisnanohoops

Chemical Science, Год журнала: 2023, Номер 14(40), С. 11121 - 11130

Опубликована: Янв. 1, 2023

In this study, we synthesized and reported the heterotopic bisnanohoops P5-[8,10]CPPs containing cycloparaphenylenes (CPPs) a pillar[5]arene unit, which act not only as energy donors but also host for binding acceptors. We demonstrated that series of elegant FRET systems could be constructed successfully through self-assembly between acceptors with different emissions via host-guest interaction. These further allow us to finely adjust (BODIPY-Br Rh-Br) achieving multiple color-tunable emissions, particularly white-light emission. More importantly, these complexes were utilized in fabrication fluorescent films integrated 365 nm LED lamp create white devices. The findings highlight new application carbon nanorings emission materials, beyond common recognition π-conjugated molecules.

Язык: Английский

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Direct Edge Functionalization of Corannulene–Coronene Hybrid Nanographenes

JACS Au, Год журнала: 2025, Номер unknown

Опубликована: Март 24, 2025

For more than a century, electrophilic aromatic substitution reactions have been central to the construction of rich variety organic molecules that are useful in all aspects human life. Typically, small nuclei, such as benzene, provide an ideal substrate. An increase number annulated rings enhances potential reactive sites and frequently results complex product mixtures. Thus, nanographenes with relatively large system seldom selective their positions. Moreover, nanographene substrates scope for multiple patterns remain rare. Herein, we demonstrate curved based on corannulene-coronene hybrid structure comprising 48 conjugated sp 2-carbon atoms allows direct regioselective edge functionalization through bromination, nitration, formylation, Friedel-Crafts acylation good yields. The postsynthetically installed functional groups can be modified versatile chemistry transformations, including (mechanochemical) Suzuki-Miyaura, Sonogashira-Hagihara, Buchwald-Hartwig amination reactions. Furthermore, substitutions carried out sequential manner yield heterofunctional structures. edge-functionalization strategy enables modular access nanostructures appealing properties, strong fluorescence emission visible near-infrared regions (475-900 nm) record Stokes shifts (>300 nm), at exceptionally carbon footprint (C48).

Язык: Английский

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Highly Luminescent Chiral Carbon Nanohoops via Symmetry Breaking with a Triptycene Unit: Bright Circularly Polarized Luminescence and Size‐Dependent Properties

Small, Год журнала: 2023, Номер 20(14)

Опубликована: Ноя. 21, 2023

Abstract Chiral carbon nanohoops with both high fluorescence quantum yield and large luminescence dissymmetry factor are essential to the development of circularly polarized (CPL) materials. Herein, rational design synthesis a series highly fluorescent chiral TP‐[8–13]CPPs via symmetry breaking triptycene motif is reported. Theoretical calculations revealed that causes unique size‐dependent localization in highest occupied molecular orbitals (HOMOs) lowest unoccupied obtitals (LUMOs) as increasing sizes, which sharply different from those [n]cycloparaphenylenes. Photophysical investigations demonstrated TP‐[n]CPPs display emissions yields up 92.9% for TP‐[13]CPP, value among reported conjugated nanohoops. The presumably attributed acyclic, radial conjugations radiative transition rates, further supported by theoretical investigations. Chiroptical studies exhibit bright CPL brightness 100.5 M −1 cm TP‐[11]CPP due yield. Importantly, intrigued properties regards (chir)optical properties, follow nice linear relationship versus 1/n. Such not observed other including CPPs.

Язык: Английский

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Chiral twisted molecular carbons: Synthesis, properties, and applications

Interdisciplinary materials, Год журнала: 2024, Номер 3(4), С. 453 - 479

Опубликована: Май 11, 2024

Abstract In recent years, the precisely controlled synthesis of chiral twisted molecular carbons has emerged as a forefront topic in research carbon materials. Molecular refer to nanomaterials synthesized with precision at atomic level. Through rational design, rigid and stable structures can be synthesized. The exploration field is key fully understanding various configurations materials delving into relationship between structure design functionality. This review explores such nanographene, nanobelts, nanosheets, graphdiyne, etc. It emphasizes role photocyclization, Scholl reaction, Diels–Alder reactions achieving precise control discusses range innovative strategies. These strategies have led development structures, helical, propeller, Möbius strip configurations. introduction chirality, combined inherent exceptional optical properties nanocarbon materials, facilitated creation superior chiroptical performances. advancement driving applications fields optoelectronics optics.

Язык: Английский

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Ultra-Narrowband Circularly Polarized Luminescence from Multiple 1,4-Azaborine-Embedded Helical Nanographenes

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(43), С. 29782 - 29791

Опубликована: Окт. 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.

Язык: Английский

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Helical β‐isoindigo‐Based Chromophores with B−O−B Bridge: Facile Synthesis and Tunable Near‐Infrared Circularly Polarized Luminescence

Angewandte Chemie International Edition, Год журнала: 2022, Номер 62(8)

Опубликована: Дек. 30, 2022

It is essential to create organic compounds that exhibit circularly polarized luminescence (CPL) in the near-infrared (NIR) range. Helicene-type emitters possess appealing chiroptical features, however, such NIR molecules are scarce due a paucity of synthetic strategies. Herein, we developed series helical β-isoindigo-based B-O-B bridged aza-BODIPY analogs were synthesized conveniently. The reaction diimino-β-isoindigo with heteroaromatic amine produced restricted ligand cavity, which triggered off generation bridge. bridge led distorted conformations satisfy requirements, resulting excellent spectroscopic and properties. Tunable CPL highest dissymmetry factor (glum ) 1.3×10-3 brightness (BCPL =11.5 M-1 cm-1 region was achieved. This approach expected offer new opportunity chiral chemistry increase flexibility for tuning.

Язык: Английский

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All Carbon Helicenes and π‐Extended Helicene Derivatives

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(12)

Опубликована: Ноя. 21, 2023

Abstract Atomic precise chiral molecules with all‐hydrocarbon backbones, such as helicenes and related π‐extended derivatives, attract critical interests due to their great application potential in many fields (e. g., optical materials, asymmetric catalysis, molecular machines). Herein, the main development of these past decade was summarizes, including enantioselective synthesis helicenes, helicene extension along perpendicular helical axis, well following both directions, namely helix axis direction.

Язык: Английский

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Chalcogen-doped, (seco)-hexabenzocoronene-based nanographenes: synthesis, properties, and chalcogen extrusion conversion

Chemical Science, Год журнала: 2023, Номер 14(33), С. 8905 - 8913

Опубликована: Янв. 1, 2023

A series of chalcogen-doped nanographenes were obtained by insertion different chalcogens into the HBC or seco -HBC backbone. The chalcogen-dependent photophysical properties and chalcogen-extrusion reactions investigated.

Язык: Английский

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A Deep‐Red Emissive Sulfur‐Doped Double [7]Helicene Photosensitizer: Synthesis, Structure and Chiral Optical Properties

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(45)

Опубликована: Авг. 8, 2024

Doping of polycyclic conjugated hydrocarbons (PCHs) with sulfur atoms is becoming more and important as a means creating unique functional materials. Recently, thiophene-containing multiple helicenes have garnered enormous attention due to their intriguing electronic (chir)optical properties compared carbohelicenes. However, the efficient synthesis thiopyran-containing underlying doping mechanisms are rather unexplored. Herein, structural analysis double [7]helicene 3 reported. X-ray crystallographic reveals its dication C

Язык: Английский

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Pyrene bridged double[7]helicene embedded with a heptagonal ring

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(15), С. 3714 - 3725

Опубликована: Янв. 1, 2023

The article explores the intricate relationship between chiroptical properties and molecular symmetry of pyrene-conjugated single double [7]helicene.

Язык: Английский

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