BN‐Anthracene for High‐Mobility Organic Optoelectronic Materials through Periphery Engineering

Abstract

Despite the remarkable synthetic accomplishments in creating diverse polycyclic aromatic hydrocarbons with B−N bonds (BN‐PAHs), their optoelectronic applications have been less exploited. Herein, we report the achievement of high‐mobility organic semiconductors based on existing BN‐PAHs through a “periphery engineering” strategy. Tetraphenyl‐ and diphenyl‐substituted BN‐anthracenes (TPBNA and DPBNA, respectively) are designed and synthesized. DPBNA exhibits the highest hole mobility of 1.3 cm2 V−1 s−1 in organic field‐effect transistors, significantly outperforming TPBNA and all the reported BN‐PAHs. Remarkably, this is the first BN‐PAH with mobility over 1 cm2 V−1 s−1, which is a benchmark value for practical applications as compared with amorphous silicon. Furthermore, high‐performance phototransistors based on DPBNA are also demonstrated, implying the high potential of BN‐PAHs for optoelectronic applications when the “periphery engineering” strategy is implemented.

Recent Advances in Boron‐Containing Acenes: Synthesis, Properties, and Optoelectronic Applications†

“…[ 85 ] To boost the device performance, recently, Wang and co‐workers proposed a “periphery engineering” strategy based on BN‐doped anthracene to achieve high‐mobility OFETs. [ 86 ] Compounds 40b and 40c were synthesized with four and two phenyl substituents, respectively (Figure 11a). The HOMO energy levels of these two compounds were determined by electrochemical measurements to be −5.25 eV and −5.28 eV, respectively.…”

BN-Embedded Cycloarenes: One-Pot Borylation Synthesis, Photoelectric Properties, and Application in Perovskite Solar Cells

“…Over the past few years, the introduction of a boron–nitrogen (B–N) covalent bond into polycyclic aromatic hydrocarbons (PAHs) has provided a novel molecular design strategy for organic semiconductors. ,,− As isoelectronicity to the CC bond, the polar B–N bond could affect the distribution of molecular orbitals, which also improves the stability of higher acenes, as previously demonstrated . The additional local dipole induced by the incorporation of B–N atoms would enhance the nonvalent intermolecular interaction, which may prompt close π–π stacking of molecules and facilitate the charge transport in the solid state. , Moreover, the electron donation of N and the electron affinity of B atoms endow BN-doped molecules with ambipolar charge trapping properties, resulting in large ambipolar memory windows in OFET memory devices . However, the complete synthesis of BN-embedded cycloarenes remains elusive, possibly due to the limitations in molecular design strategies and synthetic methods.…”

“…26 The additional local dipole induced by the incorporation of B−N atoms would enhance the nonvalent intermolecular interaction, which may prompt close π−π stacking of molecules and facilitate the charge transport in the solid state. 26,29 Moreover, the electron donation of N and the electron affinity of B atoms endow BN-doped molecules with ambipolar charge trapping properties, resulting in large ambipolar memory windows in OFET memory devices. 30 However, the complete synthesis of BN-embedded cycloarenes remains elusive, possibly due to the limitations in molecular design strategies and synthetic methods.…”

Enhanced CO2 Photoreduction through Spontaneous Charge Separation in End‐Capping Assembly of Heterostructured Covalent‐Organic Frameworks

“…[21][22][23] Owing to their excellent charge-transport properties and redox stability, they are extensively used in organic field-effect transistors, solar cells, light-emitting diodes, and photoresponsive materials. [24][25][26][27][28][29] In particular, substantial efforts have been devoted to integrating PAHs into polymers as organic semiconductors for fluorescent sensing films or singlet oxygen sensitizers. [30,31] However, to the best of our knowledge, there is no report on exploring the integration of PAHs into COFs for photocatalysis.…”

“…PAHs represent a class of molecules with multiple aromatic rings [21–23] . Owing to their excellent charge‐transport properties and redox stability, they are extensively used in organic field‐effect transistors, solar cells, light‐emitting diodes, and photoresponsive materials [24–29] . In particular, substantial efforts have been devoted to integrating PAHs into polymers as organic semiconductors for fluorescent sensing films or singlet oxygen sensitizers [30, 31] .…”