Polycyclic aromatic hydrocarbons (PAHs) and their derivatives are widely used in the field of organic optoelectronic materials, and the photophyscial properties of polycyclic aromatic hydrocarbons can be effectively modified by heteroatomic doping. By replacing carbon carbon (CC) units with an isoelectronic and isostructural boron nitrogen (BN) units, the electronic structure and intermolecular interactions of PAHs can be fine-tuned, resulting in new BN-heteroaromatics with unique optoelectronic properties and bioactivity. BN/CC isosterism can not only enrich the famlily of heteroaromatics but also promote their applications in the fields of optoelectronic, catalysis and biomedical applications. In particular, the researchers from China have engaged and promoted the development of boron/nitrogen-doped heteroaromaics, leading to some great results. The recent advance of 1,2-BN heteroaromatics in China from the chemistry perspective is summarized, including the synthetic development of 1,2-BN heteroaromatics, as well as their applications in variety of research fields. In the end, the development prospects of BN-heteroaromatics are pointed out. Through highlighting these advances of boron/nitrogen-doped heteroaromaics in China, it is hoped that more researchers will be interested in the synthesis and application of boron/nitrogen-doped heteroaromaics. It is also hoped that this review would stimulate the conversation and cooperation between the chemists and material scientists in the related fields. Keywords boron/nitrogen doped polycyclic aromatic hydrocarbon; isosterism; aromatics; organoboron chemistry 全碳稠环芳烃(PAHs)是由 sp 2 杂化碳原子组成的二 维石墨烯片段, 稠环芳烃及其衍生物由于具有独特的光 学和电子性能, 在有机光电材料领域备受科学家们的青 睐. 近几年, 以稠环芳烃为代表的有机材料在电子器件 方面应用广泛, 例如有机发光二极管(OLED)、场效应晶 体(OFET)和有机太阳能电池(OSCs) [1] . 相对于无机材 料, 有机光电材料的一个优点是可以从分子层面对其结 构进行精确改造, 从而获得所需求的性能. 在全碳稠环 芳烃的骨架中嵌入杂原子(N、S、Si、O、P 和 B 等)可 以有效调节稠环芳烃的电子结构, 进而可以调节其光电 物理性质 [2] .1919 年, 朗格缪尔(Langmuir) [3] 以 N 2 O 和 CO 2 之间 有机化学 综述与进展 1612 http://sioc-journal.cn/

Two types of "parental" BN-dibenzo[f,k]tetraphenes (BNDBT-1 and BNDBT-2) have been synthesized via a transition-metal-catalyzed tandem cross-coupling reaction as key steps. Both BNDBT-1 and BNDBT-2 are fully characterized; one of them is unambiguously confirmed by a single Xray crystal structure. Compared to its all-carbon analogue DBT, BNDBT-1 and BNDBT-2 exhibit a higher highest occupied molecular orbital (HOMO) and lower lowest unoccupied molecular orbital (LUMO) energy, while the BN doping position slightly influences the HOMO and LUMO energies of BNDBT-1 and BNDBT-2. Both BNDBT-1 and BNDBT-2 exhibit red-shifted absorption and emission spectra and higher emission efficiencies, as compared to their carbonaceous analogue DBT. Moreover, organic light emitting diodes were fabricated using BNDBT-1 and BNDBT-2 as emitters, demonstrating their potential applications.

The interaction between cysteine with Li + and LiF in the microcosmic water environment was investigated to elucidate how ions interact with amino acids and the cation–anion correlation effect involved. The structures of Cys·Li + (H 2 O) n and Cys·LiF(H 2 O) n ( n = 0–6) were characterized using ab initio calculations. Our studies show that the water preferentially interacts with Li + /LiF. In Cys·Li + (H 2 O) 0–6 , Li + interacts with amino nitrogen, carbonyl oxygen, and hydrophobic sulfur of Cys to form a tridentate mode, whereas in Cys·LiF(H 2 O) n , Li + and F – work in cooperation and interact with carbonyl oxygen and hydroxyl hydrogen of Cys to form a bidentate type. The neutral and zwitterionic forms are essentially isoenergetic when the water number reaches three in the presence of Li + , whereas this occurs at four water molecules in the presence of LiF. Further research revealed that the interaction between Li + /LiF and Cys was mainly electrostatic, followed by dispersion, and the weakest interaction occurs at the transition from the neutral form to zwitterionic form. Natural population analysis charge analyses show that for Cys·Li + (H 2 O) n , the positive charge is mostly concentrated on Li + except for the system containing three water molecules. For Cys·LiF(H 2 O) n , the positive charge is centered on the LiF unit in the range n = 0–6, and at n = 5, electron transfer from Cys to water occurs. Our study shows that the contribution of anions in zwitterionic state stabilization should be addressed more generally along with cations.

A series of bis-BN dipyrrolyl[a,j]anthracenes and a representative carbonaceous analogue have been synthesized. We studied the optical properties and OLED applications of these BN-PAHs and compared them with the carbonaceous counterpart.

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