861853-33-0Relevant academic research and scientific papers
Coronene-Containing N-Heteroarenes: 13 Rings in a Row
Endres, Alexander H.,Schaffroth, Manuel,Paulus, Fabian,Reiss, Hilmar,Wadepohl, Hubert,Rominger, Frank,Kr?mer, Roland,Bunz, Uwe H. F.
supporting information, p. 1792 - 1795 (2016/03/01)
We describe the modular synthesis of three novel large N-heteroarenes, containing 9, 11, and 13 annulated rings. This modular system features fused azaacene units to a coronene nucleus. We evaluate the optical and electronic properties and the solid-state packing of the targets. The electronic properties of the 13-ring N-heteroarene allow the fabrication of a proof-of-concept thin-film transistor. Electron mobilities up to 8 × 10-4 cm/(V s) were obtained for polycrystalline films.
Synthesis and optical properties of triphenylene-based dendritic donor perylene diimide acceptor systems
Bagui, Mahuya,Dutta, Tanmoy,Chakraborty, Sanjiban,Melinger, Joseph S.,Zhong, Haizhen,Keightley, Andrew,Peng, Zhonghua
scheme or table, p. 1579 - 1592 (2011/05/06)
A donor-acceptor charge transfer system based on two discotic mesogens has been synthesized. The donor is either a triphenylene (POG0) or a triphenylene-based conjugated dendron (POG1), while the acceptor is a perylene diimide (PDI) core. The donors are covalently linked to the bay positions of the PDI core through an ether linkage. In chloroform, due to the short donor-acceptor distance and the matching frontier orbital levels, photoinduced charge transfer from either the donor excitation or the acceptor excitation are both thermodynamically and kinetically favored, resulting in efficient quenching of both donor and acceptor fluorescence. In a less polar solvent, hexane, while charge transfer is still the dominant mechanism for decay of the excited electronic state of POG1, photoinduced charge transfer is no longer energetically favorable for POG0 when the acceptor PDI core is excited, making the PDI core of POG0 weakly fluorescent in chloroform but strongly so in hexane. In solid film, POG0 is highly aggregated through both PDI-PDI and triphenylene-triphenylene homotopic stacking. POG1, on the other hand, aggregates through triphenylene dendrons with limited PDI-PDI core stacking, presumably due to the steric hindrance caused by bulky triphenylene moieties which block the access to the PDI core. The efficient photoinduced charge transfer, coupled with the homotopic stacking that forms separated electron-transporting PDI-stacked columns and hole transporting triphenylene-stacked columns, suggests that the reported donor-acceptor systems based on dual-discotic mesogens are potentially new efficient photovoltaic materials.
One-pot facile synthesis of pyridyl annelated perylene bisimides
Jiang, Wei,Li, Yan,Yue, Wan,Zhen, Yonggang,Qu, Jianqiang,Wang, Zhaohui
supporting information; experimental part, p. 228 - 231 (2010/03/30)
(Figure presented) Two regiospecifically pyridyl annelated perylene bisimides have been prepared in one pot by the combination of the Suzuki cross-coupling reaction and subsequent light-promoted cyclization In high yields.
1,6-Disubstituted perylene bisimides: Concise synthesis and characterization as near-infrared fluorescent dyes
Fan, Liqiang,Xu, Yanping,Tian, He
, p. 4443 - 4447 (2007/10/03)
Detailed studies on bromination and subsequent imidization of perylene bisanhydride were reported. 1,6,7,12-Tetrabromoperylene bisimide was obtained in an optimized high yield. In addition, 1,6-disubstituted regioisomer was separated for the first time in isomerically pure form, and the structure was confirmed by 1H NMR, MS, element analysis, and photophysical measurements. By using a mixture of regioisomers 1,6- and 1,7-dibromo-perylene bisimide, 1,6-dipiperidinylperylene bisimides (1,6-Piper-Pery) were synthesized, purified, and their fluorescence were measured with a peak at 760 nm. These compounds can be used as stable near-infrared absorbing and fluorescent dyes.
