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π-stacking in ground-state dimers/trimers/tetramers of N-butoxyphenyl(naphthalene)diimide (BNDI) exceeds 50 kcal · mol−1 in strength, drastically surpassing that for the *3[pyrene]₂ excimer (∼30 kcal · mol−1; formal bond order = 1) and similar to other weak-to-moderate classical covalent bonds. Cooperative π-stacking in triclinic (BNDI-T) and monoclinic (BNDI-M) polymorphs effects unusually large linear thermal expansion coefficients (αₐ, αb, αc, β) of (452, −16.8, −154, 273) × 10−6 · K−1 and (70.1, −44.7, 163, 177) × 10−6 · K−1, respectively. BNDI-T exhibits highly reversible thermochromism over a 300-K range, manifest by color changes from orange (ambient temperature) toward red (cryogenic temperatures) or yellow (375 K), with repeated thermal cycling sustained for over at least 2 y.

Self‐doping has emerged as an effective strategy to tailor the electronic properties of organic materials, especially for n‐type semiconductors based on perylene diimide (PDI) and naphthalene diimide (NDI). This review summarizes recent progress in the molecular design and application of self‐doped PDI/NDI systems. Representative self‐doping groups such as amines, ammonium salts, and other anionic species are introduced and classified. The effects of doping group connecting site selection, including the imide position, aromatic core, and side substitutes, on molecular and electronic properties are then discussed. The application of self‐doped PDI/NDI materials in organic electronic devices is also highlighted, covering thin‐film solar cells, organic field‐effect transistors, and organic thermoelectrics. These materials have shown the ability to improve charge injection, enhance device stability, and regulate interfacial processes. Overall, self‐doping is a promising strategy for developing high‐performance n‐type organic semiconductors. With ongoing improvements in molecular design and device engineering, self‐doped PDI/NDI materials are expected to contribute significantly to the advancement of next‐generation electronic materials and devices. Self‐doping has emerged as an effective strategy for tailoring the electronic properties of organic materials, attracting increasing attention to PDI‐ and NDI‐based systems in recent years. This review focuses on the structural design and functional roles of self‐doped PDI/NDI materials, with particular emphasis on representative dopant groups such as amines, quaternary ammonium salts, and other functional moieties, as well as the selection of doping group connecting sites including the imide position and aromatic core. On this basis, we examine their diverse applications in organic electronic devices, including thin‐film solar cells, organic field‐effect transistors, and organic thermoelectric devices. These examples collectively highlight the strong potential of self‐doped PDI/NDI materials for enhancing carrier injection, improving device stability, and modulating interfacial processes.

Three new cadmium coordination polymers, namely [Cd(NO3)2(DPNDI)(CH3OH)]·CH3OH (1), [Cd(SCN)2(DPNDI)] (2), and [Cd(DPNDI)2(DMF)2]·2ClO4 (3) (DPNDI = N,N-di(4-pyridyl)-1,4,5,8-naphthalene diimide, DMF = N,N-dimethylformamide) have been synthesized by reactions of DPNDI with Cd(NO3)2, Cd(SCN)2, and Cd(ClO4)2, respectively. Compound 1 is a one-dimensional coordination polymer with strong lone pair-π interactions between the coordinated NO3− anions and the imide ring of DPNDI; while 2 is a two-dimensional network with a (4, 4) net topology. In the case of 3, due to the presence of uncoordinated perchlorate counter ions, it exhibits a non-interpenetrated square-grid coordination polymer containing one-dimensional rhomboid channels. The structural diversity in these compounds is attributed to different coordination abilities and geometries of counter anions. Due to the presence of electron-deficient NDI moiety, the photochromic behavior of these compounds was studied. Interestingly, only compounds 1 and 3 exhibit color changes under light irradiation. The influence of the anions on the photochromism process of the NDI-based materials has been discussed.

In organic solar cells (OSCs), cathode interfacial materials are generally designed with highly polar groups to increase the capability of lowering the work function of cathode. However, the strong polar group could result in a high surface energy and poor physical contact at the active layer surface, posing a challenge for interlayer engineering to address the trade-off between device stability and efficiency. Herein, we report a hydrogen-bonding interfacial material, aliphatic amine-functionalized perylene-diimide (PDINN), which simultaneously down-shifts the work function of the air stable cathodes (silver and copper), and maintains good interfacial contact with the active layer. The OSCs based on PDINN engineered silver-cathode demonstrate a high power conversion efficiency of 17.23% (certified value 16.77% by NREL) and high stability. Our results indicate that PDINN is an effective cathode interfacial material and interlayer engineering via suitable intermolecular interactions is a feasible approach to improve device performance of OSCs. It is desired to design cathode interfacial layers to simultaneously improve the efficiency and stability of organic solar cells and tune the cathode properties. Here, Yao et al. develop such interfacial layers for the best donor-acceptor system and achieve a high certified efficiency close to 17%.

The development of readily accessible high-mobility n-type semiconducting polymers is in great demand for realizing high-performance p-n junction-based organic electronics. In this study, we demonstrate that with the combination of dual-acceptor strategy and C-H direct arylation polymerization (DArP), unipolar n-type semiconducting polymers can be conveniently synthesized. By tuning the monomer concentration, three dual-acceptor polymers, namely, poly(naphthalene diimide- alt -dithiophenyl pyrrolopyrrole-dione) (PNDI-DPP), poly(naphthalene diimide- alt -dithiophenyl isoindigo) (PNDI-IID), and poly (naphthalene diimide- alt -dithiophenyl bezothiadiazole) (PNDI-BT) can be obtained via C-H activation with decent number average molecular weight of ∼10 to 30 kg mol −1 and relatively narrow polydispersity index of ∼2. In addition, these polymers are defect-free in nature as evidenced by the nuclear magnetic resonance. Moreover, we attribute the different molar masses of the three copolymers under the same DArP condition to the different α-C-H acidity, which may stem from different electron-withdrawing capability of the hydrogenated acceptor units. Furthermore, the influence of the hydrogenated acceptor monomers on the optical, electrochemical and charge transporting properties is comprehensively studied. Among the three dual-acceptor polymers, PNDI-BT demonstrates the highest electron mobilities of up to 0.6 cm 2 V −1 s −1 in unipolar n-type organic transistors because of its relatively planar backbone, larger overlaps of the lowest unoccupied molecular orbital and strong H-aggregation. Note that the transistor performance of PNDI-BT synthesized via C-H activation in this study is at least comparable to the one made by conventional C(sp 2 )-C(sp 2 ) Stille or Suzuki cross-coupling polymerization. This study demonstrates the presented protocol can be a useful platform for sustainable and convenient synthesis of high-performance n-type semiconducting polymers.

The synthesis of novel architecture comprising perylene diimide (PDI)-MXene (Ti 3 C 2 T X )-integrated graphitic pencil electrode for electrochemical detection of dopamine (DA) is reported. The good electron passage between PDI-MXene resulted in an unprecedented nano-adduct bearing enhanced electrocatalytic activity with low-energy electronic transitions. The anionic groups of PDI corroborated enhanced active surface area for selective binding and robust oxidation of DA, thereby decreasing the applied potential. Meanwhile, the MXene layers acted as functional conducive support for PDI absorption via strong H-bonding. The considerable conductivity of MXene enhanced electron transportation thus increasing the sensitivity of sensing interface. The inclusively engineered nano-adduct resulted in robust DA oxidation with ultra-sensitivity (38.1 μAμM −1 cm −2 ), and low detection limit (240 nM) at very low oxidation potential (−0.135 V). Moreover, it selectively signaled DA in the presence of physiological interferents with wide linearity (100–1000 μM). The developed transducing interface performed well in human serum samples with RSD (0.1 to 0.4%) and recovery (98.6 to 100.2%) corroborating the viability of the practical implementation of this integrated system. Graphical abstract Schematic illustration of the oxidative process involved on constructed sensing interface for the development of a non-enzymatic dopamine sensor.

Organic solar cells (OSCs), benefiting from their significant advantages, such as light weight, flexibility, low cost, and large area manufacturing adaptability, are considered promising clean energy technologies. Currently, the power conversion efficiency (PCE) of state‐of‐the‐art OSCs has reached over 18% through materials and device engineering. Specifically, cathode engineering with cathode interlayer materials (CIMs) is an important strategy to improve the PCEs and stability of OSCs. Among various CIMs reported in the literature, perylene diimides (PDIs) are more appropriate for working as cathode interlayers in OSCs owing to their distinct advantages of suitable energy levels, high electron affinity, high electron mobility, and facile modification. In this review, the mechanism of cathode engineering is concisely summarized, and recent research progress on PDI derivatives working as CIMs in OSCs is systematically reviewed. Finally, prospects and suggestions are provided for the development of PDI‐based CIMs for practical applications. Organic solar cells (OSCs) are considered a promising clean energy technology. Cathode engineering with cathode interlayer materials (CIMs) is an important strategy to improve the power conversion efficiency and stability of OSCs. In this review, the mechanism of cathode engineering is concisely summarized, and recent research progress on perylene diimide (PDI) derivatives working as CIMs in OSCs is systematically reviewed. Finally, prospects and suggestions are provided for the development of PDI‐based CIMs for practical applications.

In organic solar cells (OSCs), the material design on photovoltaic layers and interlayers has significantly contributed to the rapid progress of the device performance. Perylene-diimides (PDIs), owing to their distinct advantages of high electron affinity, high electron mobility and facial chemical modification, are being widely studied in OSCs, especially designed as photovoltaic acceptors and cathode interlayers. In this review, recent progress on those PDI derived photovoltaic materials is systematically summarized. Due to the different working mechanism in devices, the design strategies on modification of the parent PDI units towards their application as acceptors and cathode interlayers are explained. After disclosing the fundamental structure-property relationships, we disclose some common features in the design of those tailor-made PDI-based photovoltaic materials, and we also highlight the challenges and opportunities in improving their device performance in the future.

Pseudocapacitors harness unique charge-storage mechanisms to enable high-capacity, rapidly cycling devices. Here we describe an organic system composed of perylene diimide and hexaazatrinaphthylene exhibiting a specific capacitance of 689 F g −1 at a rate of 0.5 A g −1 , stability over 50,000 cycles, and unprecedented performance at rates as high as 75 A g −1 . We incorporate the material into two-electrode devices for a practical demonstration of its potential in next-generation energy-storage systems. We identify the source of this exceptionally high rate charge storage as surface-mediated pseudocapacitance, through a combination of spectroscopic, computational and electrochemical measurements. By underscoring the importance of molecular contortion and complementary electronic attributes in the selection of molecular components, these results provide a general strategy for the creation of organic high-performance energy-storage materials. Pseudocapacitors exhibit charge-storage mechanisms leading to high-capacity and rapidly cycling devices. An organic system designed via molecular contortion is now shown to exhibit unprecedented electrochemical performance and stability.

Precise enantiomer discrimination is crucial across diverse fields; however, developing a rapid and solvent‐free strategy for chiral discrimination is still difficult to achieve. Here, we present a chirality‐dependent Förster resonance energy transfer (FRET) system for enantiomer discrimination in the solid state. Perylene diimide (PDI) enantiomers serve as fluorescent selectands (guests), while chiral naphthalimide (NMI) or naphthalene diimide (NDI) act as chiral selectors (hosts). Photophysical studies reveal that host and guest with homochirality exhibit markedly enhanced fluorescence compared to heterochiral counterparts, attributed to more efficient FRET. In contrast, control experiments under FRET‐suppressed conditions fail to effectively discern molecular chirality. Molecular dynamics simulations reveal that homochiral host and guest tend to adopt more compact molecular packing, thereby promoting FRET. This work provides a noncovalent fluorescence‐based platform for real‐time enantioselective recognition in the solid state.