14727-71-0Relevant articles and documents
Conjugated polymers constructed by a novel pyrene-fused polycyclic building block and their applications as organic electronic materials
Wen, Hui,Gong, Xiaohui,Jia, Zhenhong,Han, Pei,Lin, Baoping,Ye, Shanghui,Sun, Ying,Zhang, Xueqin,Yang, Hong
, p. 16 - 23 (2016)
A large fused polycyclic pyrene derivative with five-membered imidazole rings fused onto pyrene core, 5,11-Bis(5-Bromothiophene-2-yl)-4,10-dioctadecyl-4,10-dihydropyreno[4,5-d:9,10- d′]diimidazole (PBTI), was designed as a new building block for the conjugated polymers. Copolymers of this monomer with vinylene (P1) and thiophene (P2) were synthesized and their physical properties and performance in organic thin film transistors were investigated. Both polymers exhibited highly coplanar backbones, similar lowest unoccupied molecular orbital energy levels at -3.7 ev and the uniform delocalized highest occupied molecular orbital with deep-lying energy levels around -5.7 ev. X-ray diffraction and grazing-incident X-ray diffraction measurements demonstrated that P2 adopted a highly ordered structure, thus giving an enhanced hole mobility of 0.015 cm2 V-1 s-1 in organic thin film transistors.
N-Rich Fused Heterocyclic Systems: Synthesis, Structure, Optical and Electrochemical Characterization
Fusco, Sandra,Maglione, Cira,Velardo, Amalia,Piccialli, Vincenzo,Liguori, Rosalba,Peluso, Andrea,Rubino, Alfredo,Centore, Roberto
, p. 1772 - 1780 (2016)
A new class of N-rich fused heterocyclic compounds containing the triazolo-triazine moiety was synthesized and studied by cyclic voltammetry, UV/Vis spectroscopy, X-ray diffraction, and first principle computations. All the compounds show reversible or quasi-reversible reduction processes, with reduction potentials easily tunable within the class. LUMO energies as low as -3.95 eV have been measured. The UV/Vis spectra show highly structured absorptions, indicative of rigid molecular skeletons. The solid-state packing is dominated by π-π stacking interactions, which are promoted by weak CAr-H···N interactions, whereas face-to-edge contacts (T contacts), typical of many fused hydrocarbons, are largely absent.
Dicyanopyrazine-containing fused aromatic molecules: Potential n-type materials for use in optoelectronic devices
Li, Qing,Li, Jiuyan,Ren, Huicai,Gao, Zhanxian,Liu, Di
, p. 3325 - 3333 (2011)
Two dicyanopyrazine-containing aromatic compounds, pyrazino[2′, 3′:9,10]phenanthro[4,5-fgh]quinoxaline-5,6,12,13-tetracarbonitrile (PPQD) and pyrazino[2′,3′:9,10]phenanthro[4,5-fgh]quinoxaline-5,6,12,13- tetracarbonitrile,2,9-bis(1,1-dimethylethyl) (PPQB), which have remarkably high electron affinity and ionization potential, were synthesized and qualified as potential n-type materials for use in solar cells and organic light-emitting diodes.
Strong Enhancement of π-Electron Donor/Acceptor Ability by Complementary DD/AA Hydrogen Bonding
Liu, Cheng-Hao,Niazi, Muhammad Rizwan,Perepichka, Dmitrii F.
, p. 17312 - 17321 (2019)
π-Conjugated organic materials possess a wide range of tunable optoelectronic properties which are dictated by their molecular structure and supramolecular arrangement. While many efforts have been put into tuning the molecular structure to achieve the desired properties, rational supramolecular control remains a challenge. Here, we report a novel series of supramolecular materials formed by the co-assembly of weak π-electron donor (indolo[2,3-a]carbazole) and acceptor (aromatic o-quinones) molecules via complementary hydrogen bonding. The resulting polarization creates a drastic perturbation of the molecular energy levels, causing strong charge transfer in the weak donor–acceptor pairs. This leads to a significant lowering (up to 1.5 eV) of the band gaps, intense absorption in the near-IR region, very short π-stacking distances (≥3.15 ?), and strong ESR signals in the co-crystals. By varying the strength of the acceptor, the characteristics of the complexes can be tuned between intrinsic, gate-, or light-induced semiconductivity with a p-type or ambipolar transport mechanism.
Solution-processable small molecule semiconductors based on pyrene-fused bisimidazole and influence of alkyl side-chain on the charge transport
Wen, Hui,Gong, Xiaohui,Han, Pei,Lin, Baoping,Zhang, Lei,Ye, Shanghui,Sun, Ying,Zhang, Xueqin,Yang, Hong
, p. 69277 - 69281 (2016)
To explore the potential of pyrene-fused biimidazole as a building block for soluble small molecule semiconductors, we designed and synthesized PBI-L-Na and PBI-B-Na. Imidazole rings provided substitution positions for the solubilising groups at the K-region, however, DFT calculations revealed that the repulsive steric hindrance from the neighboring hydrogen atoms on pyrene forced alkyl side chains into a twisted conformation. Thus, side chains on this type of molecule exerted a prominent influence on the molecular packing and affected their optoelectronic properties intensively in the solid state. PBI-L-Na exhibited a more ordered packing of the large conjugated plane with a π-π stacking distance of 0.36 nm and showed a hole mobility up to 0.12 cm2 V-1 s-1. Bulkier branched chains provided better solubility but impeded molecular packing of PBI-B-Na, thus giving a hole mobility of 4.6 × 10-3 cm2 V-1 s-1.
Ruthenium(III) chloride catalyzed oxidation of pyrene and 2,7-disubstitued pyrenes: An efficient, one-step synthesis of pyrene-4,5-diones and pyrene-4,5,9,10-tetraones
Hu, Jie,Zhang, Dong,Harris, Frank W.
, p. 707 - 708 (2005)
(Chemical Equation Presented) Pyrene and 2,7-disubstituted pyrenes have been oxidized with ruthenium(III) chloride (RuCl3) and sodium periodate (NaIO4) under very mild conditions to 4,5-diones or 4,5,9,-10-tetraones. Thus, the oxidation has been controlled by varying the amount of oxidant and reaction temperature to proceed exclusively at the pyrene 4- and 5-positions or at the 4-, 5-, 9-, and 10-positions.
An Environmentally Friendly and Flexible Aqueous Zinc Battery Using an Organic Cathode
Guo, Zhaowei,Ma, Yuanyuan,Dong, Xiaoli,Huang, Jianhang,Wang, Yonggang,Xia, Yongyao
, p. 11737 - 11741 (2018)
Rechargeable batteries have been used to power various electric devices and store energy from renewables, but their toxic components (namely, electrode materials, electrolyte, and separator) generally cause serious environment issues when disused. Such toxicity characteristic makes them difficult to power future wearable electronic devices. Now an environmentally friendly and highly safe rechargeable battery, based on a pyrene-4,5,9,10-tetraone (PTO) cathode and zinc anode in mild aqueous electrolyte is presented. The PTO-cathode shows a high specific capacity (336 mAh g?1) for Zn2+ storage with fast kinetics and high reversibility. Thus, the PTO//Zn full cell exhibits a high energy density (186.7 Wh kg?1), supercapacitor-like power behavior and long-term lifespan (over 1000 cycles). Moreover, a belt-shaped PTO//Zn battery with robust mechanical durability and remarkable flexibility is first fabricated to clarify its potential application in wearable electronic devices.
Organic Proton-Buffer Electrode to Separate Hydrogen and Oxygen Evolution in Acid Water Electrolysis
Ma, Yuanyuan,Guo, Zhaowei,Dong, Xiaoli,Wang, Yonggang,Xia, Yongyao
, p. 4622 - 4626 (2019)
Hydrogen production from water via electrolysis in acid is attracting extensive attention as an attractive alternative approach to replacing fossil fuels. However, the simultaneous evolution of H2 and O2 requires a fluorine-containing proton exchange membrane to prevent the gases from mixing while using the same space to concentrate the gases, which significantly increases the cost and reduces the flexibility of this approach. Here, a battery electrode based on the highly reversible enolization reaction of pyrene-4,5,9,10-tetraone is first introduced as a solid-state proton buffer to separate the O2 and H2 evolution of acidic water electrolysis in space and time, through which the gas mixing issue can be avoided without using any membrane. This process allows us to separately consider H2 and O2 production according to the variation in input power (e.g., the renewable energy) and/or the location for H2 concentration, thus showing high flexibility for H2 production.
Confined Spaces in [n]Cyclo-2,7-pyrenylenes
Dumele, Oliver,Grabicki, Niklas,Nguyen, Khoa T. D.,Weidner, Steffen
, p. 14909 - 14914 (2021)
A set of strained aromatic macrocycles based on [n]cyclo-2,7-(4,5,9,10-tetrahydro)pyrenylenes is presented with size-dependent photophysical properties. The K-region of pyrene was functionalized with ethylene glycol groups to decorate the outer rim and thereby confine the space inside the macrocycle. This confined space is especially pronounced for n=5, which leads to an internal binding of up to 8.0×104 m?1 between the ether-decorated [5]cyclo-2,7-pyrenylene and shape-complementary crown ether–cation complexes. Both the ether-decorated [n]cyclo-pyrenylenes as well as one of their host–guest complexes have been structurally characterized by single-crystal X-ray analysis. In combination with computational methods the structural and thermodynamic reasons for the exceptionally strong binding have been elucidated. The presented rim confinement strategy makes cycloparaphenylenes an attractive supramolecular host family with a favorable, size-independent read-out signature and binding capabilities extending beyond fullerene guests.
Synthesis, Photophysical and Electronic Properties of New Red-to-NIR Emitting Donor–Acceptor Pyrene Derivatives
Merz, Julia,Dietz, Maximilian,Vonhausen, Yvonne,W?ber, Frederik,Friedrich, Alexandra,Sieh, Daniel,Krummenacher, Ivo,Braunschweig, Holger,Moos, Michael,Holzapfel, Marco,Lambert, Christoph,Marder, Todd B.
, p. 438 - 453 (2020)
We synthesized new pyrene derivatives with strong bis(para-methoxyphenyl)amine donors at the 2,7-positions and n-azaacene acceptors at the K-region of pyrene. The compounds possess a strong intramolecular charge transfer, leading to unusual properties such as emission in the red to NIR region (700 nm), which has not been reported before for monomeric pyrenes. Detailed photophysical studies reveal very long intrinsic lifetimes of >100 ns for the new compounds, which is typical for 2,7-substituted pyrenes but not for K-region substituted pyrenes. The incorporation of strong donors and acceptors leads to very low reduction and oxidation potentials, and spectroelectrochemical studies show that the compounds are on the borderline between localized Robin-Day class-II and delocalized Robin-Day class-III species.
