Recent advances in n-type and ambipolar organic semiconductors and their multi-functional applications

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(4), P. 1331 - 1381

Published: Jan. 1, 2023

A comprehensive summary and deep insights into the synthesis, characterization multi-functional device applications of n-type ambipolar organic semiconductors are provided in this study.

Language: Английский

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13% Single‐Component Organic Solar Cells based on Double‐Cable Conjugated Polymers with Pendent Y‐Series Acceptors

Advanced Materials, Journal Year: 2023, Volume and Issue: 35(18)

Published: Feb. 23, 2023

Double-cable conjugated polymers with pendent electron acceptors, including fullerene, rylene diimides, and nonfused have been developed for application in single-component organic solar cells (SCOSCs) efficiencies approaching 10%. In this work, Y-series acceptors firstly incorporated into double-cable order to further improve the of SCOSCs. A highly crystalline acceptor based on quinoxaline core random copolymerized strategy are used optimize ambipolar charge transport nanophase separation polymers. As a result, an efficiency 13.02% is obtained polymer, representing highest performance SCOSCs, while regular polymer only provides low 2.75%. The significantly enhanced attributed higher carrier mobilities, better ordering backbones

Language: Английский

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Naphthalimide-Annulated [n]Helicenes: Red Circularly Polarized Light Emitters

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(17), P. 9886 - 9894

Published: April 21, 2023

Two [n]heliceno-bis(naphthalimides) 1 and 2 (n = 5 6, respectively) where two electron-accepting naphthalimide moieties are attached at both ends of helicene core were synthesized by effective two-step strategy, their enantiomers could be resolved chiral stationary-phase high-performance liquid chromatography (HPLC). The single-crystal X-ray diffraction analysis enantiopure fractions confirmed helical structure, together with experimental calculated circular dichroism (CD) spectra, the absolute configuration was unambiguously assigned. Both exhibit high molar extinction coefficients for S0–S1 transition fluorescence quantum yields (73% 69% 2), being outstanding derivatives. red circularly polarized luminescence (CPL) emission up to 615 nm CPL brightness (BCPL) 66.5 M–1 cm–1 demonstrates its potential applications in optoelectronics. Time-dependent density functional theory (TD-DFT) calculations showed that large magnetic dipole moment |m| is responsible absorbance dissymmetry (gabs) (glum) factor.

Language: Английский

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Synthesis of π-Conjugated Chiral Organoborane Macrocycles with Blue to Near-Infrared Emissions and the Diradical Character of Cations

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(18), P. 10092 - 10103

Published: April 26, 2023

Highly emissive π-conjugated macrocycles with tunable circularly polarized luminescence (CPL) have sparked theoretical and synthetic interests in recent years. Herein, we report a approach to obtain new chiral organoborane (CMC1, CMC2, CMC3) that are built on the structurally [5]helicenes highly luminescent triarylborane/amine moieties embedded into cyclic systems. These rarely accessible B/N-doped main-group show unique topology dependence of optoelectronic chiroptical properties. CMC1 CMC2 higher dissymmetry factor (glum) together an enhanced CPL brightness (BCPL) as compared CMC3. Electronic effects were also tuned resulted bathochromic shifts their emission responses from blue for near-infrared (NIR) region Furthermore, chemical oxidations N donor sites gave rise stable radical cation (CMC1·+SbF6–) diradical dication species (CMC12·2+2SbF6–) serve rare example positively charged open-shell macrocycle.

Language: Английский

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Molecular design and architectonics towards film-based fluorescent sensing

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(13), P. 6960 - 6991

Published: Jan. 1, 2024

This review meticulously traces the development of film-based fluorescent sensors, spotlighting key advancements in molecular design and film structural engineering.

Language: Английский

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Molecular Design of Perylene Diimide Derivatives for Photocatalysis

ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 1829 - 1840

Published: Jan. 17, 2025

Perylene diimides (PDIs) and their derivatives represent a kind of most promising photocatalytic materials due to strong visible light absorption, ease functionalization, excellent thermal/photostability, as well tunable electronic structures energy levels. However, several challenges persist in the development PDI photocatalysts, including low electron–hole separation efficiency, slow charge transfer, rapid carrier recombination. In this perspective, we focus on enhancing performance photocatalysts through molecular design. We provide comprehensive overview various improvement strategies: (1) precise modulation dipole moments by altering polarity side chains strengthen built-in electric field, (2) utilization steric hindrance noncovalent interactions construct nanoscale, highly ordered supramolecular nanostructures, (3) modification perylene core adjust levels increase number active sites, (4) integration with semiconductors or metals form composite systems that enhance interfacial field create extensive delocalized channels, (5) selection suitable linker groups build polymer large moments. These strategies can facilitate migration photogenerated carriers eventually boosting efficiency. The relationship between structure performance, particularly context degradation water splitting, is examined detail. Finally, future prospects are thoroughly discussed.

Language: Английский

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Molecular Carbons: How Far Can We Go?

ACS Nano, Journal Year: 2023, Volume and Issue: 17(21), P. 20734 - 20752

Published: Oct. 27, 2023

The creation and development of carbon nanomaterials promoted material science significantly. Bottom-up synthesis has emerged as an efficient strategy to synthesize atomically precise nanomaterials, namely, molecular carbons, with various sizes topologies. Different from the properties feasibly obtained mixture numerous single-component carbons have been discovered owing their well-defined structures well potential applications in fields. This Perspective introduces recent advances derived fullerene, graphene, nanotube, carbyne, graphyne, Schwarzite acquired different strategies. By selecting a variety representative examples, we elaborate on relationship between nanomaterials. We hope these multiple points view presented may facilitate further advancement this field.

Language: Английский

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Red Emissive Double Aza[7]helicenes with Antiaromaticity / Aromaticity Switching via the Redox‐Induced Radical Cation and Dication Species

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(18)

Published: March 6, 2023

We herein present the synthetic approach to a new antiaromatic double aza[7]helicene C that features NN-embedded polycyclic aromatic hydrocarbons (PAHs). This heteroatom-doped helicene showed rarely obtained long-wavelength emission and far-red circularly polarized luminescence (CPL) in solid state. These optical chiroptical properties could be ascribed both NN-PAH core structure further extension through angular ring fusions. Such unique electronic also culminated facile chemical oxidations of neutral positively charged chiral radical (C⋅+ ) dication species (C2+ ). Interestingly, DFT computations revealed pyridazine central an antiaromaticity-to-aromaticity switching, contrast inversed transition for helical periphery cationic states. The reported approaches are anticipated lead development redox-active systems potential applications chiroptoelectronics, spintronics as well fluorescent bioimaging.

Language: Английский

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n‐Type Glycolated Imide‐Fused Polycyclic Aromatic Hydrocarbons with High Capacity for Liquid/Solid‐Electrolyte‐based Electrochemical Devices

Advanced Functional Materials, Journal Year: 2023, Volume and Issue: 33(22)

Published: Feb. 26, 2023

Abstract Currently, n‐type small‐molecule mixed ionic‐electronic conductors remain less explored and their molecular design rules are not mature enough. Herein, two glycolated imide‐fused polycyclic aromatic hydrocarbons (IPAHs), d‐gdiPDI t‐gdiPDI, developed to probe the effects of conformation on electronic, electrochemical, morphological, coupled transport properties. It is found that highly twisted scaffold in d‐gdiPDI, compared nearly planar one has a strong positive effect charge storage properties thus performance organic electrochemical transistors (OECTs). exhibits volumetric capacitance 657 F cm −3 , obviously outperforming t‐gdiPDI (261 ), which highest value reported date for OECT materials. Moreover, high charge‐storage capacity up 479 g −1 observed d‐gdiPDI. Arising from such coupling characteristic, d‐gdiPDI‐based OECTs present ≈2 × times higher geometry‐normalized transconductance ( m,norm ) 105.3 mS relative counterparts. Significantly, further application solid‐electrolyte delivers 142.4 . These findings indicate IPAHs very promising candidates highlight superiority twisting manipulation materials toward high‐performance devices.

Language: Английский

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π-Extended Helical Multilayer Nanographenes with Layer-Dependent Chiroptical Properties

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(49), P. 26824 - 26832

Published: Dec. 4, 2023

Helical nanographenes (NGs) have attracted increasing attention recently because of their intrinsic chirality and exotic chiroptical properties. However, the efficient synthesis extended helical NGs featuring a multilayer topology is still underdeveloped, layer-dependent properties remain elusive. In this study, we demonstrate modular synthetic strategy to construct series novel (1-3) with through consecutive Diels-Alder reaction regioselective cyclodehydrogenation from readily accessible phenanthrene-based precursors bearing ethynyl groups. The resultant exhibit bilayer, trilayer, tetralayer structures elongated π extension rigid backbones, as unambiguously confirmed by single-crystal X-ray or electron diffraction analysis. We find that photophysical these are notably influenced degree extension, which varies number layers, leading obvious redshifted absorption, fast rising molar extinction coefficient (ε), markedly boosted fluorescence quantum yield (Φf). Moreover, embedded [7]helicene subunits in result stable chirality, enabling both chiral resolution exploration Profiting good alignment electric magnetic dipole moments determined structure, excellent circular dichroism circularly polarized luminescence response unprecedented high CPL brightness up 168 M-1 cm-1, rendering them promising candidates for emitters.

Language: Английский

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