BN‐Embedded Tetrabenzopentacene: A Pentacene Derivative with Improved Stability

Abstract

Considerable efforts have been devoted to achieving stable acene derivatives for electronic applications; however, the instability is still a major issue for such derivatives. To achieve higher stability with minimum structural change, CC units in the acenes were replaced with isoelectronic BN units to produce a novel BN‐embedded tetrabenzopentacene (BNTBP). BNTBP, with a planar structure, is highly stable to air, moisture, light, and heat. Compared with its carbon analogue tetrabenzopentacene (TBP), BN embedment lowered the highest occupied molecular orbital (HOMO) energy level of BNTBP, changed the orbital distribution, and decreased the HOMO orbital coefficients at the central carbon atoms, which stabilize BNTBP molecules upon exposure to oxygen and sunlight. The single‐crystal microribbons of BNTBP exhibited good performance in field‐effect transistors (FETs). The high stability and good mobility of BNTBP indicates that BN incorporation is an effective approach to afford stable large‐sized acenes with desired properties.

BN Fused Diazulenyl‐Carbazole: Synthesis, Structure, and Properties

“…[ 1‐4 ] Replacing the unpolarized carbon‐carbon double bond with its isoelectronic, polarized boron‐nitrogen single bond could induce significant changes in molecular orbital distribution, energy levels, and reactivity. [ 5‐10 ] This strategy enables the development of novel heteroaromatics with favorable molecular packing and optoelectronic properties, endowing them with wide applications in organic optoelectronic devices, such as organic field‐effect transistors (OFETs), [ 11‐15 ] organic solar cells (OSCs), [ 16‐18 ] organic light‐ emitting diodes (OLEDs), [ 19‐21 ] and sensing platforms. [ 22 ] Although BN‐fused PAHs were first synthesized 60 years ago, innovative molecular design and their synthesis have remained challenging and become the bottleneck of the field.…”

B,N-Embedded Double Hetero[7]helicenes with Strong Chiroptical Responses in the Visible Light Region

“…31 Among various heterohelicenes and multiple heterohelicenes, only a few examples involving both boron (B) and nitrogen (N) atoms have been developed by employing either B-N covalent bonds or B→N coordinate bonds. [32][33][34][35][36][37] In view of the growing interest in B,N-doped PAHs as novel π-conjugated materials with intriguing optoelectronic properties, [38][39][40][41][42] B,N-incorporated (multiple) heterohelicenes have seemingly been underexplored, with the reported gabs only on the order of 10 -3 . [33][34][35] Figure 1.…”

From a 1,2-azaborinine to largeBN-PAHsviaelectrophilic cyclization: synthesis, characterization and promising optical properties

“…22,23 Moreover, fluorescence in the visible spectrum 24,25 in PAHs such as pyrenes 26,27 or perylene diimides 28,29 made them widely used, semiconducting materials in organic electronics like organic light emitting diodes (OLEDs). 30,31 Over the past decade, the incorporation of one or more 1,2-azaborinine units into PAHs has gained increased interest because the resulting BN-PAHs feature several beneficial qualities: Compared to their CC analogs, narrowed frontier molecular orbital gaps with particularly stabilized highest occupied molecular orbitals (HOMOs) [32][33][34][35] as well as redshifted emission spectra 36 could be observed. Moreover, quantum yields up to unity 37,38 and hole mobilities up to 0.15 cm 2 V -1 s -1 39 emphasize the application potential of BN-PAHs.…”