The narrowest armchair graphene nanoribbon (AGNR) with five carbons across the width of GNR (5-AGNR) was synthesized on Au(111) surfaces via sequential dehalogenation processes in a mild condition by using 1,4,5,8-tetrabromonaphthalene as molecular precursor. Gold-organic hybrids were observed high-resolution scanning tunneling microscopy and considered intermediate states upon AGNR formation. Scanning spectroscopy reveals an unexpectedly large band gap Δ = 2.8 ± 0.1 eV surface which can be...

Organic near-infrared (NIR) photoblinking fluorophores are highly desirable for live-cell super-resolution imaging based on single-molecule localization microscopy (SMLM). Herein we introduce a novel small chromophore, PMIP, through the fusion of perylenecarboximide with 2,2-dimetheylpyrimidine. PMIP exhibits an emission maximum at 732 nm high fluorescence quantum yield 60% in wavelength range 700–1000 and excellent without any additives. With resorcinol-functionalized (PMIP-OH), NIR SMLM...

The self-assembly of an amphiphilic monomolecular electron acceptor–donor dyad into electroactive π–π stacked fibrillar structures can be triggered by irradiation with visible light. These fibers, exposing hydrophilic ethylene glycol in their external shell, show unique characteristics as resistive humidity sensors that exhibit high sensitivity and ultrafast response.

Biocompatible organic dyes emitting in the near-infrared are highly desirable fluorescence imaging techniques. Herein we report a synthetic approach for building novel small peri-guanidine-fused naphthalene monoimide and perylene chromophores. The presented structures possess absorption emission, high photostability, good water solubility. After fast cellular uptake, they selectively stain mitochondria with low background live fixed cells. They can be additionally modified one-step reaction...

An efficient method to synthesize 3,4,9,10-tetrabromoperylenes is reported under optimized Hunsdiecker conditions. Various octasubstituted perylenes were obtained by reaction of 1,6,7,12-tetrachloro-3,4,9,10-tetrabromoperylene with phenol, trimethylsilyl chloride, cooper cyanide, or sulfur via metal-catalyzed couplings nucleophilic substitutions. These new show completely different optical and redox properties, thus opening a facile way develop chromophophore structures.

Synthetic models of the active site [FeFe]-hydrogenase containing naphthalene monoimide (NMI) peri-substituted dichalcogenides as bridging linkers have been prepared and characterized using different spectroscopic methods. The influence imide functionality chalcogen atoms on redox properties catalytic behaviour complexes 7-10 was studied cyclic voltammetry. results revealed that has improved chemical stability reduced species replacement S by Se caused a cathodic shift in oxidation peaks....

The nature of the bridging dithiolate has an important role on tuning physical and electrochemical properties synthetic H-cluster mimics [FeFe]-hydrogenase still significant concern to scientists. In this report we describe models active site containing perylene monoimide peri-substituted disulfides as linker. resulting complexes were characterized by 1H 13C{1H} NMR IR spectroscopic techniques, mass spectrometry, elemental analysis well X-ray complex 2a. purpose work was investigate...

An efficient synthesis of 9,10-dibromo-1,6,7,12-tetrachloro-perylene-3,4-dicarboxylic acid monoimides from easily available 1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic dianhydride is reported. Therefrom, unprecedented perylene with pronounced donor–acceptor character were obtained via twofold aromatic amination. The halogen substituents in the 1,6,7,12-positions removed under basic conditions. To best our knowledge, this first synthetic route toward 9,10-doubly functionalized...

Schematic illustration of the twisted π-conjugated system strategy to achieve enhanced fluorescence emission and ROS generation efficiency.

In recent years, bipolar organic electrode materials have gained recognition as competitive alternatives to inorganic due their unique multielectron redox mechanism for energy storage. this study, we examined the of reactions in naphthalimide (NI) derivatives when used electrodes lithium half-cells with ionic liquid electrolytes. The NI consist three building fragments: an aromatic naphthalene core, N-alkylated imide unit, and a peri-dichalcogenide bridge. integration electrochemical...

Abstract Soluble ultra‐narrow armchair graphene nanoribbons (AGNRs) with length of ≈20 nm and completely fused cores exceeding 5 in length, pronounced near‐infrared (NIR) absorption up to 1400 nm, a low band gap (≈0.9 eV) are synthesized from 3,9(3,10)‐dibromoperylene 3,4,9,10‐tetrabromoperylene. Since the monomers obtained perylene carboxyanhydrides, remarkable link between dye chemistry is established. The two‐step protocol for AGNR synthesis by aryl–aryl coupling subsequent...

A series of π-extended cycl[3,3,2]azines (3) bearing additional carbonyl groups were synthesized via aldol condensations. Two strong electron acceptor molecules (4 and 5), with low-lying LUMO energy levels −3.99 −3.95 eV, respectively, obtained. Organic thin-film transistors (TFTs) based on the cyanated cyclazine derivatives 5 fabricated by vapor deposition, exhibiting extraordinarily stable n-type semiconductor character under ambient condition highest mobility 0.06 cm2 V–1 s–1 consistently...

Abstract In this work, we present a new synthetic strategy for fourfold‐substituted perylene monoimides via tetrabrominated monoanhydrides. X‐ray diffraction analysis unveiled the intramolecular stacking orientation between substituents and semicircular packing behavior. We observed remarkable influence of substituent on longevity nature excited state upon visible light excitation. presence poly(dehydroalanine)‐graft‐poly(ethylene glycol) graft copolymers as solubilizing template,...

A useful and straightforward synthetic approach to afford heteroarenes by symmetrical annulation of two benzofuran units 1,8-naphthalene anhydrides, through a regioselective one-pot Sn–Ar/C–H activation tandem reaction is introduced herein. Two pathways are compared, highlighting that the utilization diester derivatives improves: (i) compatibility with key ring expansion step, (ii) solubility intermediate thus facilitating its purification, (iii) versatility final imidization. The...

The solid-state supramolecular organization of asymmetric perylene diimide is transformed from helical to layered self-assembly after thermal annealing.

In the search for bipolar organic materials as electrodes in rechargeable batteries, we report peri-diselenolo-substituted 1,8-naphthalimides (NIs). The molecular architecture consists of structural motifs comprising a naphthalimide core, peri-diselenide...

Controlling the nanoscale morphology of organic thin films represents a critical challenge in fabrication (opto)electronic devices. The (multicomponent) turn depends on mutual orientation molecular components and their supramolecular packing surface. Here, it is shown how surface co-assembly electron-donating -accepting building blocks can be controlled via (supra)molecular design. Hexa-peri-hexabenzocoronene (HBC) derivatives with multiple hydrogen-bonding (H-bonding) sites were synthesized...

A facile and efficient synthesis of benzo[<italic>kl</italic>]acridines was developed based on a domino reaction <italic>via</italic> combinatorial catalyst approach.

Blue organic light-emitting diodes (OLED) suffer from relatively short lifetimes and a comparatively low lighting efficiency. One of the approaches to improving their characteristics is development luminophores with potential for thermally activated delayed fluorescence (TADF). Herein, set donor-spacer-acceptor compounds TADF are designed, synthesized, computationally spectroscopically characterized. The excited state dynamics most prospective dye monitored by time-resolved transient...

Computational modeling of the optical characteristics organic molecules with potential for thermally activated delayed fluorescence (TADF) may assist markedly development more efficient emitting materials light-emitting diodes. Recent theoretical studies in this area employ mostly methods from density functional theory (DFT). In order to obtain accurate predictions within approach, choice a proper is crucial. current study, we focus on testing performance set DFT functionals estimation...

A new class of near-infrared (NIR) fluorophores, PAI, is obtained by consecutive C-N/C-C bond formation between diphenylamines and 9,10-dibromoperylenecarboximide. Owing to the rigid structure, extended π-conjugation pronounced push-pull substitution, these fluorophores show emission maxima up 804 nm large Stokes shifts. The extraordinarily high fluorescence quantum yields from 47 % 70 are attributed chloro substitution in bay positions perylene core. These characteristics, together with...

Nowadays, organosulfur compounds provide new options in the development of full organic ion batteries. However, many drawbacks (such as kinetics limitations during reversible oxidation disulfides with cleavage S–S bond, well solubility non-aqueous electrolytes) make their commercialization difficult. Herein, a concept for design regulated redox properties and limited is proposed. As proof-of-concept, we designed peri-disulfo-substituted 1,8-naphthalimide derivatives, which alkyl chain length...

Benzothioxanthene imide (BTI) has recently emerged as an interesting and promising block for organic electronics. In this contribution, we report on the impact of N-annulation latter dye optoelectronic π-extended molecular structures. To do so, thiophene-diketopyrrolopyrrole was selected, central π-conjugated core, either end-capped with two BTIs or its N-annulated version, namely TCI. While almost similar band gaps were measured individual rylene dyes, significant differences highlighted,...