2019
DOI: 10.1021/jacs.9b01082
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Three-Dimensional Pyrene-FusedN-Heteroacenes

Abstract: Four three-dimensional (3D) pyrene-fused N -heteroacenes ( P1 – P4 ) are designed and synthesized. From P1 to P4 , their lengths are extended in an iterative way, where the thiadiazole unit can be reduced to diamine and the obtained diamines can be further condensed with the diketones with a thiadiazole unit. Compared to their two-dimensional counterparts, the solubility of these 3D pyrene-fused … Show more

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Cited by 45 publications
(39 citation statements)
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References 51 publications
(106 reference statements)
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“…If the heteroatom is sp 2 nitrogen, these materials are called N-heteroacenes. [6] The chemistry and structures of PAHs and N-heteroacenes have been attracting wide interest in the community of chemistry, materials and theoretical science. [7] In the past decades, they have been explored as active components in organic light-emitting diodes (OLEDs), [8] organic field-effect transistors (OFETs), [9] memory devices, [10] sensors, [11] energy storage [12] and photovoltaic devices (OPVs).…”
Section: Introductionmentioning
confidence: 99%
“…If the heteroatom is sp 2 nitrogen, these materials are called N-heteroacenes. [6] The chemistry and structures of PAHs and N-heteroacenes have been attracting wide interest in the community of chemistry, materials and theoretical science. [7] In the past decades, they have been explored as active components in organic light-emitting diodes (OLEDs), [8] organic field-effect transistors (OFETs), [9] memory devices, [10] sensors, [11] energy storage [12] and photovoltaic devices (OPVs).…”
Section: Introductionmentioning
confidence: 99%
“…By this approach, soluble PFPs with up to 22 fused rings could be synthesized. Its diameter is approximately 11 nm, which is up to date the largest soluble N‐heteroacene derivative [19] . PFPs combine high stability with desirable electronic properties, [20] that can further be tuned by appropriate substituents, [21] making them versatile target compounds for materials used for a wide spectrum of applications, including organic field‐effect transistors (OFETs), [21g, 22] organic light emitting diodes (OLEDs) [23] or photovoltaic cells [22e, 23c, d, g, 24] …”
Section: Introductionmentioning
confidence: 99%
“…While there are examples for triptycene‐based PFPs, [19, 25] planar, star shaped PFPs [26] or phenylene bridged PFP dimers, [27] no TBTQ based analogue has been realized so far.…”
Section: Introductionmentioning
confidence: 99%
“…Among the developed organic functional materials, nitrogen‐doped acenes have emerged as an important platform for high‐performance organic electronics. [ 38–43 ] Their properties can be feasibly modulated by the number/valence/position of nitrogen atoms, which afford possibilities of achieving exceptional solid‐state microstructures and optoelectronic properties. [ 39,43 ] To date, nitrogen‐doped acenes have demonstrated to be promising candidates for various fields such as organic solar cells (OSCs), [ 42,44 ] organic field‐effect transistors (OFETs), [ 43,45 ] and organic light‐emitting diodes (OLEDs).…”
Section: Introductionmentioning
confidence: 99%