Correction: Recent progress of core-substituted naphthalenediimides: highlights from 2010.

Correction for 'Recent progress of core-substituted naphthalenediimides: highlights from 2010' by Sheshanath V. Bhosale et al., Org. Biomol. Chem., 2012, 10, 6455-6468, https://doi.org/10.1039/C2OB25798J.

Fabrication of Mesoporous Materials Based on Supramolecular Self-Assembly of Guanosine Monophosphonate-Nickel Chloride (GMP-Ni) for High-Performance Hybrid Supercapacitors.

Supramolecular self-assembly of nickel chloride and guanosine mono-phosphonate (GMP) and nickel (Ni)-based GMP-Ni and their calcinated mesoporous electrode materials GMP-Ni-500 and GMP-Ni-700 at 500 and 700 °C, respectively, have been fabricated. GMP-Ni, GMP-Ni-500, and GMP-Ni-700 are examined for their supercapacitor performance in a three-electrode configuration. The electrochemical tests demonstrate the mesoporous battery-type nature of GMP-Ni-500 which exhibited a specific capacity (Cs) of about 289 C g-1 at 0.5 A g-1 current density. In addition, a cost-effective and simple asymmetric supercapacitor device has been fabricated with battery-type GMP-Ni-500 as a cathode material and capacitive-type activated carbon (AC) as an anodic material. In an operating voltage window of 0 to 1.5 V, hybrid supercapacitors (HSCs) based on GMP-Ni-500//AC exhibited a remarkable performance with a specific capacity (Cs) of 144 C g-1 at 0.5 A g-1. For the HSC device, the maximum of 66% capacity retention has been observed after 5000 charging/discharging cycles at 5 A g-1. Furthermore, the HSC device demonstrates a high energy density of 24 W h kg-1 at a power density of 297 W kg-1. The molecular transformation was established by employing theoretical calculations. These results suggest that our HSC has outstanding potential in technology development for next-generation commercial applications.

Synthesis, Photophysical Properties and Self-Assembly of a Tetraphenylethylene-Naphthalene Diimide Donor-Acceptor Molecule.

The development of new π-conjugated molecular structures with controlled self-assembly and distinct photophysical properties is crucial for advancing applications in optoelectronics and biomaterials. This study introduces the synthesis and detailed self-assembly analysis of tetraphenylethylene (TPE) functionalized naphthalene diimide (NDI), a novel donor-acceptor molecular structure referred to as TPE-NDI. The investigation specifically focuses on elucidating the self-assembly behavior of TPE-NDI in mixed solvents of varying polarities, namely chloroform: methylcyclohexane (CHCl3 : MCH) and chloroform: methanol (CHCl3 : MeOH). Employing a several analytical methodologies, including UV-Vis absorption and fluorescence emission spectroscopy, scanning electron microscopy (SEM), X-ray diffraction (XRD), and dynamic light scattering (DLS), these self-assembled systems have been comprehensively examined. The results reveal that TPE-NDI manifests as distinct particles in CHCl3 : MCH (fMCH =90 %), while transitioning to flower-like assemblies in CHCl3 : MeOH (fMeOH =90 %). This finding underscores the critical role of solvent polarity in dictating the morphological characteristics of TPE-NDI self-assembled aggregates. Furthermore, the study proposes a molecular packing mechanism, based on SEM data, offering significant insights into the design and development of functional supramolecular systems. Such advancements in understanding the molecular self-assembly new π-conjugated molecular structures are anticipated to pave the way for novel applications in material science and nanotechnology.

Donor-acceptor molecular architecture involving carbazole/pyrazine/anthraquinone units for efficient supercapacitor applications.

A donor-acceptor composed of two 3,6-di-tert-butyl-9H-carbazoles (DTCs) and fused pyrazine (Pyz; 1)-anthraquinone (AQ; 1) was successfully synthesized. The as-fabricated DTCz-Pyz-AQ/graphite foil (GF) electrode in supercapacitor (SC) applications exhibited excellent specific capacitance (Csp) of about 304. 37 F g-1 and 106.0 F g-1 at 0.5 A g-1 current density in three electrode and symmetric two electrode configurations of SC cells, respectively, accompanied by good cycling stability. The highest energy density of the SSC cell was found to be 15.94 W h kg-1 at 899.71 W kg-1 power density. As a proof of concept DTCz-Pyz-AQ/GF (D-A/GF) has great potential in energy storage (ES) applications.

Retraction: Hydrogen sulfate ion sensing in aqueous media based on a fused pyrimido benzothiazole derivative.

[This retracts the article DOI: 10.1039/C6RA01980C.].

Retraction: Dipyrrolyl-bis-sulfonamide chromophore based probe for anion recognition.

[This retracts the article DOI: 10.1039/C4RA04000G.].

Retraction: A phosphonic acid appended naphthalene diimide motif for self-assembly into tunable nanostructures through molecular recognition with arginine in water.

Retraction of 'A phosphonic acid appended naphthalene diimide motif for self-assembly into tunable nanostructures through molecular recognition with arginine in water' by Kamalakar P. Nandre et al., Chem. Commun., 2013, 49, 5444-5446, https://doi.org/10.1039/C3CC41259H.

2H-Pyran-2-one-Functionalized Diketopyrrolopyrrole Dye: Design, Synthesis, and Explosives Sensor.

In this work, a 2H-pyran-2-one-functionalized diketopyrrolopyrrole (DPP) (coded as receptor 1) was designed, synthesized, and fully characterized by various spectroscopic methods. The physical properties of molecular architecture 1 were studied employing theoretical calculations. Receptor 1 was elegantly scrutinized for the sensing of explosive nitroaromatic compounds (NACs). Receptor 1 exhibited detection of nitro explosives, i.e., picric acid (PA), 2,4-dinitrophenol (DNP), and nitrophenol (NP), via the fluorescence quenching mechanism. The Stern-Volmer equation was employed to evaluate the effectiveness of the quenching process. It was found that 1 exhibited a detection limit of about 7.58 × 10-5, 8.35 × 10-5, and 9.05 × 10-5 M toward PA, DNP, and NP, respectively. The influence of interfering metal ions and anions on PA detection was investigated thoroughly. Furthermore, receptor 1-based low-cost fluorescent thin-layer chromatography (TLC) plates were developed for the recognition of PA.

Direct Arylation: A Greener Synthesis of Anthraquinone-Naphthalene diimide-Based Small Chromophores for Applications in Organic Thin Film Transistors.

In this paper, we report the design and synthesis of three naphthalene diimide- (NDI) and anthraquinone- (AQ) based organic chromophores derived from direct arylation reactions; NDI-AQ, AQ-NDI-AQ and NDI-AQ-NDI. Compared to classic cross-coupling reactions, this method reduced the number of synthetic and purification steps. The chemical structures, photophysical and electrochemical properties of these molecules were characterized using UV-vis spectroscopy, fluorescence emission spectroscopy and cyclic voltammetry (CV). The optoelectronic properties of the three dyes enabled the fabrication of organic thin film transistors (OTFTs). The fabricated OTFTs displayed good n-type semiconducting properties, with electron mobilities ( µ e ${{\mu }_{e}}$ ) of 1.5-4.2×10-4  cm2  V-1 s-1 .

Aminoglycoside antibiotic kanamycin functionalized tetraphenylethylene molecular probe for highly selective detection of bovine serum albumin protein.

A novel tetraphenylethylene (TPE) functionalized aminoglycoside antibiotic kanamycin (TPE-kana 1) has been successfully synthesized and characterized by means of modern analytical and spectroscopic techniques. The probe TPE-kana 1 showed strong affinity towards bovine serum albumin (BSA) compared to its other biological competitors. The recognition of BSA have been investigated employing UV-Vis absorption and fluorescence emission spectroscopy. The significant color change of TPE-kana 1 with BSA can be observed by necked eye, where the role of AIE-active TPE molecule is handle in both optical and colorimetric changes. The quenching of fluorescence of TPE-kana 1 with BSA was characterized by fluorescence spectroscopy, with 71.16% of quenching efficiency. Moreover, the Stern-Volmer quenching constant was calculated and found to be 2.46 × 107 M-1. Probe TPE-kana 1 showed detection limit of 2.87 nM (nM) towards BSA with binding constant 7.56 × 107 M. A molecular docking study is also performed to investigate the detail interactions between TPE-kana 1 with the sites of BSA via non-covalent i.e., H-bonding, π-cation interactions, π-donor hydrogen bonds and π-π interactions. The lowest binding energy conformation was found at - 10.42 kcal/mol.

Correction: Dipyrrolyl-bis-sulfonamide chromophore based probe for anion recognition.

[This corrects the article DOI: 10.1039/C4RA04000G.].

Host-Assisted Aggregation-Induced Emission of a Tetraphenylethylene Derivative and Its Responses toward External Stimuli.

Aggregation-induced emission (AIE) of fluorogenic dyes offers many opportunities as smart materials, fluorescence sensing of analytes, bioimaging, molecular electronics, and many others. AIE dyes (called AIEgens) produce emission through aggregation, which are more advantageous than conventional emission of monomeric fluorophores, as the latter is unduly susceptible toward various quenching processes. Here, we report AIE enhancement of a polyanionic sulfonato-tetraphenylethylene (SuTPE) derivative, achieved through supramolecularly assisted dye aggregation, as SuTPE interacts with a multicationic amino-ß-cyclodextrin (AßCD) host. Aggregation of the dye is induced mainly because of strong electrostatic interaction of SuTPE with AßCD, causing a significant extent of charge neutralization for the polyanionic dyes, helping their assemblage at the multicationic host portal. Job's plot studies suggest preferential formation of 2:1 dye-to-host stoichiometric complexes in the present system. Ionic-strength-dependent studies nicely support the involvement of electrostatic interaction in the present system through salt-induced disintegration of the SuTPE-AßCD complexes. The AIE enhancement for the SuTPE-AßCD system is very sensitive to the external stimuli, such as pH and temperature, suggesting its prospects in various stimuli-responsive applications. Furthermore, the SuTPE-AßCD system can suitably quantify an important bioanalyte, ATP, following a competitive binding strategy, suggesting its potential application as a supramolecular biosensor.

Conjoint use of Naphthalene Diimide and Fullerene Derivatives to Generate Organic Semiconductors for n-type Organic Thin Film Transistors.

In this paper, we described the design, synthesis, and characterization of two novel naphthalene diimide (NDI) core-based targets modified with terminal fullerene (C60 ) yield - so called S4 and S5, in which NDI bearing 1 and 2 molecules of C60 , respectively. The absorption, electrochemical and thin-film transistor characteristics of the newly developed targets were investigated in detail. Both S4 and S5 displayed broad absorption in the 450-500 nm region, owing to the effect of conjugation due to fullerene functionalities. The electrochemical measurement suggested that the HOMO and the LUMO energy levels can be altered with the number of C60 units. Both S4 and S5 were employed as organic semiconductor materials in n-channel transistors. The thin film transistor based on S4 exhibited superior electron mobility (µe) values ranging from 1.20×10-4 to 3.58×10-4  cm2  V-1 s-1 with a current on-off ratio varying from 102 to 103 in comparison with the performance of S5 based transistor, which exhibited µe ranging from 8.33×10-5 to 2.03×10-4  cm2  V-1 s-1 depending on channel lengths.

An ATP responsive fluorescent supramolecular assembly based on a polyelectrolyte and an AIE active tetraphenylethylene derivative.

Aggregation induced emission (AIE) active probes have attracted enormous attention due to their wide-spread and ever increasing number of applications in the sensing of chemically and biologically important molecules. AIE probes undergo drastic modulation in their photophysical features from a monomeric to aggregated state. In the current work, we report the aggregation of tetra-anionic Su-TPE (AIE active probe) in the presence of a cationic polyelectrolyte, poly(allylaminehydrochloride) (PAH). A supramolecular assembly is formed by the electrostatic interaction between cationic PAH and anionic Su-TPE molecules, which leads to drastic modulations in the spectral features of anionic Su-TPE upon addition of cationic PAH. The Su-TPE-PAH aggregate assembly has been investigated using various photophysical techniques, such as, ground-state absorption, steady-state and time-resolved emission spectroscopic techniques along with 1H NMR measurements. The Su-TPE-PAH aggregate assembly is found to be responsive towards the ionic strength of the medium and temperature which results in drastic modulations of the spectral features of the emissive supramolecular aggregate assembly. Finally, the specific recognition of an important bioanalyte, ATP, has been achieved using the formed Su-TPE-PAH supramolecular aggregate assembly as a sensing platform which displays good selectivity and high sensitivity towards ATP. Importantly, the developed sensor platform could also function in the human serum matrix, hence, demonstrating the potential of the established sensor platform for real-life applications in near future.

Molecular Aggregation of Naphthalene Diimide(NDI) Derivatives in Electron Transport Layers of Inverted Perovskite Solar Cells and Their Influence on the Device Performance.

One of key factors to design applicable electron transport layers (ETLs) for perovskite solar cells is the morphology of ETLs since a good morphology would help to facilitate the carrier transport at two interfaces (perovskite\ETL and ETL\cathode). However, one drawback of most organic ETL small molecules is the internal undesired accumulation, which would cause the formation of inappropriate morphology and rough ETL surface. Here, by elaborately designing the side chains of NDI derivatives, the molecular interaction could be modified to achieve the aggregation in different degrees, which would eventually affect the accumulation of molecules and surface qualities of ETLs. By speculating from the comparison between the absorption spectra of solutions and films, the sequence of extent of molecule interaction and aggregation was built among three NDI derivatives, which is further confirmed by direct evidence of atomic force microscopy (AFM) images. Then, carrier exaction abilities are simply studied by steady-state photoluminescence spectroscopy. The carrier transport process is also discussed based on cyclic voltammetry, time-resolved photoluminescence spectroscopy and mobility. NDIF1 are proven to have the appropriate internal aggregation to smooth the contact with cathode and low series resistance, and a device performance of 15.6 % is achieved. With the ability of preventing the thermal diffusion of Ag towards the perovskite surface due to the strong interaction between molecules, NDIF2 at high concentration shows the highest fill factor (80 %).

Influences of Structural Modification of Naphthalenediimides with Benzothiazole on Organic Field-Effect Transistor and Non-Fullerene Perovskite Solar Cell Characteristics.

Developing air-stable high-performance small organic molecule-based n-type and ambipolar organic field-effect transistors (OFETs) is very important and highly desirable. In this investigation, we designed and synthesized two naphthalenediimide (NDI) derivatives (NDI-BTH1 and NDI-BTH2) and found that introduction of 2-(benzo[d]thiazol-2-yl) acetonitrile groups at the NDI core position gave the lowest unoccupied molecular orbital (LUMO; -4.326 eV) and displayed strong electron affinities, suggesting that NDI-BTH1 might be a promising electron-transporting material (i.e., n-type semiconductor), whereas NDI-BTH2 bearing bis(benzo[d]thiazol-2-yl)methane at the NDI core with a LUMO of -4.243 eV was demonstrated to be an ambipolar material. OFETs based on NDI-BTH1 and NDI-BTH2 have been fabricated, and the electron mobilities of NDI-BTH1 and NDI-BTH2 are 14.00 × 10-5 and 8.64 × 10-4 cm2/V·s, respectively, and the hole mobility of NDI-BTH2 is 1.68 × 10-4 cm2/V·s. Moreover, a difference in NDI-core substituent moieties significantly alters the UV-vis absorption and cyclic voltammetry properties. Thus, we further successfully employed NDI-BTH1 and NDI-BTH2 as electron transport layer (ETL) materials in inverted perovskite solar cells (PSCs). The PSC performance exhibits that NDI-BTH2 as the ETL material gave higher power conversion efficiency as compared to NDI-BTH1, that is, NDI-BTH2 produces 15.4%, while NDI-BTH1 gives 13.7%. The PSC performance is comparable with the results obtained from OFETs. We presume that improvement in solar cell efficiency of NDI-BTH2-based PSCs is due to the well-matched LUMO of NDI-BTH2 toward the conduction band of the perovskite layer, which in turn increase electron extraction and transportation.

Supramolecular super-helix formation via self-assembly of naphthalene diimide functionalised with bile acid derivatives.

The design of chiral chromophores that lead to self-assembly of higher order helical structures is a powerful tool to understand the hierarchical helical structures of molecules of nature. In this work, we present a self-assembled helical super-structure produced via facial stacking of a bile acid bolaamphiphile derivative with a naphthalene diimide core (NDI-DCA), driven by solvophobic effects in THF-H2O solvent mixtures. The chirality of the helical microstructure is directed by the multiple chiral centres in the precursor molecule. The chirality of the hierarchical assemblies was observed using circular dichroism (CD), Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) measurements. We propose that the NDI-DCA super-structures are formed via similar interactions and mechanisms to those observed in biological molecules such as proteins and DNA.

Antenna-like Ring Structures via Self-Assembly of Octaphosphonate Tetraphenyl Porphyrin with Nucleobases.

Supramolecular self-assembly of an octaphosphonate tetraphenyl porphyrin with three different nucleobases (adenine, cytosine, and thymine) was studied. Porphyrin 1 with 8 and 10 equiv of cytosine produces light-harvesting ring-like structures, that is, architectures similar to those observed in natural light-harvesting antenna. However, porphyrin assembled with adenine or thymine resulted in prisms and microrods, respectively. UV-vis absorption, fluorescence, and dynamic light scattering were used to determine the mode of aggregation in solution. Scanning electron microscopy and X-ray diffraction spectroscopy used to visualize the self-assembled nanostructures and their behavior in the solid state, respectively. Thus, we believe that this study may demonstrate a deeper understanding on how one needs to manipulate donor/acceptor subunits in supramolecular assemblies to construct artificial antenna architectures.