Nature Energy, Published online: 24 June 2024; doi:10.1038/s41560-024-01558-y
A high-performance ternary organic solar cell (OSC) is developed through rational design of a nonfullerene guest acceptor. The optimized single-junction OSC shows reduced photon and carrier losses, leading to a high power conversion efficiency of more than 20%.Shared posts
Single-junction organic solar cells with a power conversion efficiency of more than 20%
Synthesis of Closed‐Heterohelicenes Interconvertible between Their Monomeric and Dimeric Forms
![Synthesis of Closed-Heterohelicenes Interconvertible between Their Monomeric and Dimeric Forms](https://onlinelibrary.wiley.com/cms/asset/24f62e59-bfcf-42ab-bc95-4db8a3dc976a/anie202314968-toc-0001-m.png)
The oxidation of closed-[7]helicenes with [bis(trifluoroacetoxy)iodo]benzene gave the corresponding dimers connected at the β-positions of the pyrrole units through a remarkably elongated C−C bond of about 1.60 Å. Homolytic bond dissociation took place upon UV irradiation to reform its monomeric form. The interconversion between monomeric and dimeric forms is associated with a turn-on of circularly polarized luminescence.
Abstract
Oxidative fusion reaction of cyclic heteroaromatic pentads consisting of pyrrole and thiophene gave closed-heterohelicene monomers and dimers depending on the oxidation conditions. Specifically, oxidation with [bis(trifluoroacetoxy)iodo]benzene (PIFA) gave closed-[7]helicene dimers connected at the β-position of one of the pyrrole units with remarkably elongated C−C bonds of about 1.60 Å. Although this bond was intact against thermal and physical activations, homolytic bond dissociation took place in DMSO upon irradiation with UV light to give the corresponding monomers. Thus, interconversion between the closed-helicene monomer and dimer was achieved. The optically pure dimer was photo-dissociated into the monomers associated with a turn-on of circularly polarized luminescence (CPL).
Publisher Correction: Doubly N-confused and ring-contracted [24] hexaphyrin Pd-complexes as stable antiaromatic N-confused expanded porphyrins
Nature Communications, Published online: 31 August 2023; doi:10.1038/s41467-023-41072-5
Publisher Correction: Doubly N-confused and ring-contracted [24] hexaphyrin Pd-complexes as stable antiaromatic N-confused expanded porphyrinsSelf‐Doped n‐Type Quinoidal Compounds with Good Air Stability and High Electrical Conductivity for Organic Electronics
![Self-Doped n-Type Quinoidal Compounds with Good Air Stability and High Electrical Conductivity for Organic Electronics](https://pericles.pericles-prod.literatumonline.com/cms/asset/8b2d57b5-dc98-468e-ac12-33896d2d17a6/anie202307856-toc-0001-m.png)
A closed-shell quinoidal backbone has been used to develop self-doped n-type conductive molecules (QnNs) with high electrical conductivities and good air stability. Intermolecular electron transfer from the amino groups to the quinoidal backbone was found to result in the self-doping. Applying the QnNs as the cathode interlayer (CIL) in organic solar cells led to an outstanding power conversion efficiency (PCE) of up to 18.2 %.
Abstract
Air stable n-type conductive molecules with high electrical conductivities and excellent device performance have important applications in organic electronics, but their synthesis remains challenging. Herein, we report three self-doped n-type conductive molecules, designated QnNs, with a closed-shell quinoidal backbone and alkyl amino chains of different lengths. The QnNs are self-doped by intermolecular electron transfer from the amino groups to the quinoidal backbone. This process is ascertained unambiguously by experiments and theoretical calculations. The use of a quinoidal structure effectively improves the self-doping level, and thus increases the electrical conductivity of self-doped n-type conductive molecules achieved by a closed-shell structure from<10−4 S cm−1 to>0.03 S cm−1. Furthermore, the closed-shell quinoidal structure results in good air stability of the QnNs, with half-lives>73 days; and Q4N shows an electrical conductivity of 0.019 S cm−1 even after exposure to air for 120 days. When applying Q6N as the cathode interlayer in organic solar cells (OSCs), an outstanding power conversion efficiency of up to 18.2 % was obtained, which represents one the best results in binary OSCs.
[ASAP] Cyclic Homo- and Heterohalogen Di‑λ3‑diarylhalonium Structures
[ASAP] Enantiopure J‑Aggregate of Quaterrylene Bisimides for Strong Chiroptical NIR-Response
The Regioselective Solid‐State Photo‐Mechanochemical Synthesis of Nanographenes with UV light
![The Regioselective Solid-State Photo-Mechanochemical Synthesis of Nanographenes with UV light](https://onlinelibrary.wiley.com/cms/asset/8b2a1885-4cd2-46a7-a03e-adb91183f64b/anie202218719-toc-0001-m.png)
Photochemistry and mechanochemistry have been combined to synthesize nanographenes in the complete absence of bulk solvents. The concept is showcased with two reactions—the Mallory reaction and the cyclodehydrochlorination, both applicable to the intramolecular formation of C−C bonds. Moreover, the approach can even form these bonds regioselectively in larger systems—something not possible before in mechanochemistry.
Abstract
Photochemical reactors inherently suffer from the low penetration depth of light and therefore rely on high dilutions to enable chemical reactions. Here we present the first method of UV (ultraviolet) photochemistry in the complete absence of bulk solvents in a ball mill. Triphenylene was synthesized by two routes, the Mallory reaction and the cyclodehydrochlorination (CDHC), resulting in yields of 81 and 92 %, respectively. The reaction was successfully scaled up to the gram scale and the robustness of the method was demonstrated for several different substrates. Finally, the regioselective assembly of nanographenes by mechanochemistry was demonstrated for larger systems. Thus, the mechanochemical approach presented here provides a powerful new tool for the atomically precise construction of nanographenes.
[ASAP] Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Palladium-Catalyzed Asymmetric Intramolecular C–H Arylations
Reversible Handedness Inversion and Circularly Polarized Light Reflection Tuning in Self‐Organized Helical Superstructures Using Visible‐Light‐Driven Macrocyclic Chiral Switches
![Reversible Handedness Inversion and Circularly Polarized Light Reflection Tuning in Self-Organized Helical Superstructures Using Visible-Light-Driven Macrocyclic Chiral Switches](https://onlinelibrary.wiley.com/cms/asset/c89e3166-a0b3-4000-b576-3562511d5e84/anie202216600-toc-0001-m.png)
The synthesized macrocyclic chiral photoswitches are capable of reversible photoisomerization driven by visible light. The photoswitches show enhanced helical twisting power (HTP) in liquid crystals and diverse HTP changes upon photoisomerization. The photoswitches with shorter substituents enable visible-light-driven handedness inversion of the self-assembled helical superstructures.
Abstract
A series of macrocyclic azobenzene-based chiral photoswitches have been judiciously designed, synthesized, and characterized. In the molecular structures, binaphthyl is covalently linked to ortho-positions of azobenzene, and four different substituents are linked to 6,6′-positions of binaphthyl. The photoswitches show enhanced helical twisting power (HTP) when doping in commercially available achiral liquid crystals to form self-organized helical superstructures, i.e., cholesteric liquid crystals (CLCs). All the photoswitches exhibit reversible photoisomerization driven by visible light of different wavelengths in both organic solvent and liquid crystals. The photoswitches with shorter substituents enable handedness inversion of CLCs upon photoisomerization. These are the first examples of ortho-linked azobenzene-based photoswitches that enable handedness inversion in CLCs. The photoswitches with longer substituents display only HTP values decreasing while maintaining the same handedness.
[ASAP] Alkyl-Substituted N,S-Embedded Heterocycloarenes with a Planar Aromatic Configuration for Hosting Fullerenes and Organic Field-Effect Transistors
Recent Progress in Printable Organic Field Effect Transistors
DOI: 10.1039/C8TC05485A, Review Article
Printable organic field effect transistors (OFETs) have been investigated for more than 20 years, aiming at various emerging applications including flexible/wearable electronics, displays and sensors. Since many comprehensive review articles...
The content of this RSS Feed (c) The Royal Society of Chemistry
Competition between Exceptionally Long‐Range Alkyl Sidechain Ordering and Backbone Ordering in Semiconducting Polymers and Its Impact on Electronic and Optoelectronic Properties
![Advanced Functional Materials Competition between Exceptionally Long‐Range Alkyl Sidechain Ordering and Backbone Ordering in Semiconducting Polymers and Its Impact on Electronic and Optoelectronic Properties](https://onlinelibrary.wiley.com/cms/attachment/2bc3c8ca-5019-4628-b956-48f3882703bb/adfm201806977-gra-0001-m.png)
A crystalline alkyl sidechain phase with coherence lengths >70 nm is reported in a series of representative semiconducting polymers. This ordering induces backbone disorder, revealing competing forces of the backbone and sidechain that prevent simultaneous ordering of both the constituents. Implications for molecular design that facilitates synergistic long‐range crystallization are discussed.
Abstract
Intra‐ and intermolecular ordering greatly impacts the electronic and optoelectronic properties of semiconducting polymers. The interrelationship between ordering of alkyl sidechains and conjugated backbones has yet to be fully detailed, despite much prior effort. Here, the discovery of a highly ordered alkyl sidechain phase in six representative semiconducting polymers, determined from distinct spectroscopic and diffraction signatures, is reported. The sidechain ordering exhibits unusually large coherence lengths (≥70 nm), induces torsional/twisting backbone disorder, and results in a vertically multilayered nanostructure with ordered sidechain layers alternating with disordered backbone layers. Calorimetry and in situ variable temperature scattering measurements in a model system poly{4‐(5‐(4,8‐bis(3‐butylnonyl)‐6‐methylbenzo[1,2‐b:4,5‐b′]dithiophen‐2‐yl)thiophen‐2‐yl)‐2‐(2‐butyloctyl)‐5,6‐difluoro‐7‐(5‐methylthiophen‐2‐yl)‐2H‐benzo[d][1,2,3]triazole} (PBnDT‐FTAZ) clearly delineate this competition of ordering that prevents simultaneous long‐range order of both moieties. The long‐range sidechain ordering can be exploited as a transient state to fabricate PBnDT‐FTAZ films with an atypical edge‐on texture and 2.5× improved field‐effect transistor mobility. The observed influence of ordering between the moieties implies that improved molecular design can produce synergistic rather than destructive ordering effects. Given the large sidechain coherence lengths observed, such synergistic ordering should greatly improve the coherence length of backbone ordering and thereby improve electronic and optoelectronic properties such as charge transport and exciton diffusion lengths.
Pyrene-fused PDI based ternary solar cells: high power conversion efficiency over 10%, and improved device thermal stability
DOI: 10.1039/C8QM00486B, Research Article
A class of pyrene-fused PDI-NFAs are designed and synthesized for fabricating ternary OSC devices to improve the absorption in the short wavelength region, VOC and thermal stability of the ternary devices.
The content of this RSS Feed (c) The Royal Society of Chemistry
[ASAP] Chemical and Biomolecule Sensing with Organic Field-Effect Transistors
Response to Comment on “Charge Carrier Extraction in Organic Solar Cells Governed by Steady‐State Mobilities”
K-Y1
Comment on “Charge Carrier Extraction in Organic Solar Cells Governed by Steady‐State Mobilities”
K-Y1
[ASAP] Upgrading Cross-Coupling Reactions for Biaryl Syntheses
K-Y1
[ASAP] The History of Palladium-Catalyzed Cross-Couplings Should Inspire the Future of Catalyst-Transfer Polymerization
K-Y1
Why are S–F and S–O non-covalent interactions stabilising?
K-Y=
DOI: 10.1039/C8TC04252G, Paper
Dipole alignment of substituents greatly affects the torsional potential between neighbouring rings in conjugated organic materials.
The content of this RSS Feed (c) The Royal Society of Chemistry
[ASAP] Controlled Polymerization of a Cyclopentadithiophene–Phenylene Alternating Copolymer
[ASAP] Thiophene–Vinylene–Thiophene-Based Donor–Acceptor Copolymers with Acetylene-Inserted Branched Alkyl Side Chains To Achieve High Field-Effect Mobilities
Carbonyl-Functionalized Cyclazines as Colorants and Air-Stable n-Type Semiconductors
Titanocene-Mediated Dinitrile Coupling: A Divergent Route to Nitrogen-Containing Polycyclic Aromatic Hydrocarbons
A Stable Blue Photosensitizer for Color Palette of Dye-Sensitized Solar Cells Reaching 12.6% Efficiency
Fluorescent Cyanine Dye J-Aggregates in the Fluorous Phase
A Direct C–H Coupling Method for Preparing π-Conjugated Functional Polymers with High Regioregularity
K-Y🍊
Aromaticity switching via azulene transformations in azulene-bridged A,D-dithiahexaphyrin
DOI: 10.1039/C7CC08754C, Communication
The incorporation of an azulene bridge into an aromatic hexaphyrin framework allows to manipulate [small pi]-electron delocalization pathways. The palladium(II) complex undergoes the hydroxyl-triggered azulene contraction or isomerization to an oxynaphthalene...
The content of this RSS Feed (c) The Royal Society of Chemistry
[small pi]-Conjugation expanded isoindigo derivatives and the donor-acceptor conjugated polymers: synthesis and characterization
DOI: 10.1039/C7CC08603B, Communication
Two [small pi]-conjugation expanded isoindigo derivatives (DIID-PhCO and TIID-PhCO) composed of up to 18 rings and two donor-acceptor conjugated polymers based on DIID-PhCO were synthesized. Both polymers are ambipolar semiconductors with...
The content of this RSS Feed (c) The Royal Society of Chemistry