Ke Shi

A Non‐Fullerene Small Molecule as Efficient Electron Acceptor in Organic Bulk Heterojunction Solar Cells

A novel n-type small molecule FFI-1 was synthesized as the electron acceptor to replace PCBM in solution-processed organic BHJ solar cells. Its LUMO level (around -3.5 eV) both matches the work function of the cathode and increases V(OC) of the devices, making it a promising acceptor candidate. With P3HT: FFI-1 (1:2 w/w) as active layer and LiF/Al as the cathode, the best power conversion efficiency (PCE) reaches 1.86%.

Toward High Performance n-Type Thermoelectric Materials by Rational Modification of BDPPV Backbones

Three n-type polymers BDPPV, ClBDPPV, and FBDPPV which exhibit outstanding electrical conductivities when mixed with an n-type dopant, N-DMBI ((4-(1,3-dimethyl-2,3-dihydro-1H-benzoimidazol-2-yl)phenyl)dimethylamine), in solution. High electron mobility and an efficient doping process endow FBDPPV with the highest electrical conductivities of 14 S cm(-1) and power factors up to 28 μW m(-1) K(-2), which is the highest thermoelectric (TE) power factor that has been reported for solution processable n-type conjugated polymers. Our investigations reveal that introduction of halogen atoms to the polymer backbones has a dramatic influence on not only the electron mobilities but also the doping levels, both of which are critical to the electrical conductivities. This work suggests the significance of rational modification of polymer structures and opens the gate for applying the rapidly developed organic semiconductors with high carrier mobilities to thermoelectric field.

A bowl-shaped molecule for organic field-effect transistors: crystal engineering and charge transport switching by oxygen doping

A corannulene-based derivative was facilely developed with a bowl-shaped structure. Highly ordered cofacial convex–concave stacking was realized through tuning the molecular dipoles, which is favorable for charge transport. Organic field-effect transistors were fabricated, providing opportunities for a broad class of corannulene derivatives and buckybowl aromatics for application in future organic electronic devices.

Corannulene derivatives as non-fullerene acceptors in solution-processed bulk heterojunction solar cells

Corannulene derivatives were used in organic solar cells for the first time. Using Cor-PI and Cor-NI as acceptors, we achieved power conversion efficiencies up to 0.32% and 1.03%, suggesting potential applications of these fullerene segments as non-fullerene acceptors.

Fusion at the non-K-region of pyrene: an alternative strategy to extend the π-conjugated plane of pyrene.

A large fused pyrene derivative TTTP was facilely developed through fusion at the non-K-region of pyrene, which represents the first example of extending such a π-conjugated plane at its non-K-region. The investigation of its photophysical properties and other characterizations indicated that TTTP exhibited strong aggregation behaviors and self-assembled into highly ordered one-dimensional nanowires due to its large π-conjugated plane.

Enhanced Molecular Packing of a Conjugated Polymer with High Organic Thermoelectric Power Factor

The detailed relationship between film morphology and the performance of solution processed n-type organic thermoelectric (TE) devices is investigated. It is interesting to find that the better ordered molecular packing of n-type polymer can be achieved by adding a small fraction of dopant molecules, which is not observed before. The better ordered structure will be favorable for the charge carrier mobility. Meanwhile, dopant molecules improve free carrier concentration via doping reaction. As a result, a significantly enhanced electrical conductivity (12 S cm(-1)) and power factor (25.5 μW m(-1) K(-2)) of TE devices are obtained. Furthermore, the phase separation of conjugated polymer/dopants is observed for the first time with resonant soft X-ray scattering. Our results indicate that the miscibility of conjugated polymers and dopants plays an important role on controlling the morphology and doping efficiency of TE devices.

π-Conjugated aromatics based on truxene: synthesis, self-assembly, and applications

Recently, many efforts have been devoted to developing novel polycyclic aromatics due to their unique optical and electronic properties and broad applications, such as in organic field-effect transistors, organic photovoltaics, and organic light-emitting diodes. Among various π-conjugated molecules, many truxene derivatives have interesting characteristics such as C3 -symmetry, strong blue emission, and a planar rigid structure. Moreover, compared with many other π-conjugated aromatics, the synthesis and modification of truxene are particularly facile and diverse. In this account, we summarize investigations into truxene derivatives from synthesis and physical properties to applications in organic electronics.

5,5′-Diazaisoindigo: an Electron-Deficient Building Block for Donor–Acceptor Conjugated Polymers

A novel electron-deficient building block, 5,5-diazaisoindigo (5DNIID), was synthesized through a facile method in good yield. As a derivative of isoindigo, 5DNIID shows an ultra-low LUMO level of -3.92u2005eV after incorporation of two electron-deficient nitrogen atoms into the para-position of the amine groups in the isoindigo π skeleton. Modified polymerization conditions were applied to efficiently afford the donor-acceptor (D-A) conjugated polymer 5DNIID-2T, which exhibited a p-type charge transport property.

Syntheses of polycyclic aromatic diimides via intramolecular cyclization of maleic acid derivatives

Using readily available aryl glyoxylic acids and arylene diacetic acids as starting materials, a series of polycyclic aromatic molecules bearing two phthalimide functional groups are synthesized via Perkin condensation followed by intramolecular cyclization reactions. Two different cyclization methods, photo-oxidation and Heck cross-coupling, are employed, both of which effectively accomplish the transformations from diaryl maleic anhydride or maleimide to polycyclic aromatic phthalimide functionality. The photocyclization protocol conveniently allows direct bridging of two plain aromatic C–H sites linked by a maleic anhydride group and uniquely produces the more twisted polycyclic framework as the major product, whereas the Heck coupling approach can typically afford more extended polycyclic skeletons. Thionation reactions are then carried out for the obtained polycyclic diimide molecules using Lawessons reagent. For all isolated stable products, partial thionation occurs. The prepared polycyclic diimide compounds possess relatively low LUMO levels, and thionation further decreases the LUMO energy of the molecules by 0.2–0.3 eV. Electron-transporting properties are characterized by using solution-processed OFET devices, and an electron mobility of 0.054 cm2 V−1 s−1 is demonstrated by a selected compound. Such semiconducting performance promises great potentials of this class of compounds as useful electron-accepting and transporting building blocks in developing various new semiconductive materials.

Epindolidione-Based Conjugated Polymers: Synthesis, Electronic Structures, and Charge Transport Properties.

Development of new electron-deficient building blocks is essential to donor-acceptor conjugated polymers. Herein, epindolidione (EPD) as electron-deficient unit was integrated into conjugated polymers for the investigation of field-effect transistors for the first time. We systematically studied the electronic structures and charge transport properties of the EPD-based donor-acceptor polymers. They exhibit p-type transport characteristics with the highest mobility of up to 0.40 cm(2) V(-1) s(-1), thus demonstrating its great potential as a building block for polymer field-effect transistors and photovoltaics.