5737-13-3Relevant academic research and scientific papers
Investigation of thresholds in laser-induced carbonization of sumanene derivatives through in situ observation utilizing a Raman spectroscope
Inada, Yuhi,Amaya, Toru,Hirao, Toshikazu
, p. 18523 - 18530 (2015)
A useful method was demonstrated to investigate 532 nm laser energy threshold to carbonize various compounds including sumanene derivatives through in situ observation utilizing a micro-Raman spectrometer. It was revealed that the thresholds of sumanene derivatives are lower than those of the planar partial structures of sumanene derivatives. Moreover, [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) shows a considerably lower threshold than the sumanene derivatives utilizing this method. This work can be expected to contribute toward the evolution of laser-induced carbonization-based chemistry.
A Three-Step Synthesis of 4H-Cyclopenta[def]phenanthrene from Pyrene
Filippov, Dmitri V.,Overkleeft, Hermen S.,Schneider, Grégory F.,van der Ham, Alex
supporting information, p. 2013 - 2017 (2021/06/25)
4H-Cyclopenta[def]phenanthrene (CPP) is a valuable building block in the production of photoactive polymers, which find use in a wide range of organic electronic applications. Of particular importance is their use in the development of blue-colored, organic light-emitting diodes (OLEDs), which remains a challenge in the field. Unfortunately, commercial sources and synthetic procedures known in the literature are unable to provide enough CPP for large scale implementation. Herein, we report on the development of a novel, gram-scale synthesis of CPP in three steps, starting from pyrene. The key steps in our methodology are the ring contraction of pyrene-4,5-dione to oxoCPP in a single step, as well as the direct reduction of oxoCPP to CPP. Apart from the small number of synthetic steps, our methodology benefits from the use of relatively non-hazardous reagents, together with optimized purification procedures, making CPP accessible in useful quantities.
Contorted tetrabenzoacenes of varied conjugation: Charge transport study with single-crystal field-effect transistors
Huang, Ding-Chi,Kuo, Chi-Hsien,Ho, Man-Tzu,Lin, Bo-Chao,Peng, Wei-Tao,Chao, Ito,Hsu, Chao-Ping,Tao, Yu-Tai
supporting information, p. 7935 - 7943 (2017/08/17)
A series of contorted and polyfused aromatic tetrabenzoacene derivatives differing in conjugation length were synthesized and characterized. X-ray diffraction revealed the contorted molecular shape, as well as the packing arrangement of these molecules. Thus unsubstituted tetrabenzoacenes showed a shifted or perfect face-to-face π-stacking depending on their conjugation length. The single crystals of these tetrabenzoacenes were used as conducting channels in fabricating field-effect transistors (SCFETs). Tetrabenzotetracene (TBT) exhibited the highest measured mobility, approaching 0.81 cm2 V-1 s-1 (average 0.64 cm2 V-1 s-1) among these molecules. In contrast, theoretical calculation showed that the tetrabenzooctacene (TBO) crystal has large-area, face-to-face π-packing, with the highest intermolecular coupling in the series. The lower charge mobility (average 0.32 cm2 V-1 s-1, highest 0.55 cm2 V-1 s-1) observed was rationalized as a result of possible involvement of delocalized polaron formation due to comparable electronic coupling and reorganization energy in TBO, as supported by the Monte Carlo simulation with this delocalized effect taken into account.
High open circuit voltage organic photovoltaic cells fabricated using 9,9′-bifluorenylidene as a non-fullerene type electron acceptor
Kim, Hee Un,Kim, Ji-Hoon,Suh, Hongsuk,Kwak, Jeonghun,Kim, Dongwook,Grimsdale, Andrew C.,Yoon, Sung Cheol,Hwang, Do-Hoon
supporting information, p. 10950 - 10952 (2013/11/19)
We have found that 9,9′BF can be used as an electron acceptor for P3HT-based OPVs while similar devices using 4,4′BP do not show any photovoltaic effect. This can be related to the respective aromaticity and antiaromaticity of the reduced forms of 9,9′BF or 4,4′BP. The OPV device fabricated using P3HT and 9,9′BF exhibited a PCE of 2.28% with a Voc of 1.07 V, a Jsc of 5.04 mA cm-2, and a FF of 0.42. The Royal Society of Chemistry 2013.
Energy transfer in bichromophoric molecules: The effect of symmetry and donor/acceptor energy gap
Yip,Levy, Donald H.,Kobetic, Renata,Piotrowiak, Piotr
, p. 10 - 20 (2007/10/03)
The dependence of the rate of singlet excitation transfer on the donor-acceptor energy gap was investigated in bichromophoric spiranes with symmetry-forbidden zero-order electronic coupling. The fluorescence measurements were performed in a supersonic jet in order to avoid collisional and inhomogeneous line broadening. Fluorescence excitation spectra and single-vibronic-level emission spectra of the model chromophores cyclopentaphenanthrene and 1,8-dimethylnaphthalene and the bichromophores spirofluorenephenanthrene and spirofluorenenaphthalene are presented and analyzed. Although the transition moments of the linked chromophores are rigorously perpendicular and the exchange coupling between the v′ = 0 states is computationally shown to be zero, all spiranes with energy gaps larger than ～1000 cm-1 exhibited complete electronic energy transfer from all vibrational states of the electronically excited donor, including the undistorted v′ = 0 state. This behavior is explained in terms of vibronic coupling between the sparse states of the donor and the dense manifold (pseudocontinuum) of the acceptor states. The electronic energy transfer was sufficiently fast to result in measurable lifetime broadening of the donor absorption lines, from which the kEET was estimated. The results demonstrate that the zero-order picture overestimates the degree of the molecular orbital symmetry control over electronic energy transfer and charge-transfer rates and that at sufficiently high driving forces the vibronically mediated "symmetry-forbidden" electronic energy transfer can be very rapid (～1 × 1012 s-1).
Synthesis of Ketone and Alcohol Derivatives of Methylene-Bridged Polyarenes, Potentially New Classes of Active Metabolites of Carcinogenic Hydrocarbons
Harvey, Ronald G.,Abu-shqara, Elias,Yang, ChengXi
, p. 6313 - 6317 (2007/10/02)
Methods for the syntheses of bridge ketone and alcohol derivatives of methylene-bridged polyarenes from the parent hydrocarbons are described.The polyarenes investigated include 4H-cyclopentaphenanthrene (1a), fluorene (2a), 7H-benzofluorene (3a), 4H-cyclopentachrysene (4a), 11H-benzaceanthrylene (5a), 10H-indenopyrene (6a), 11H-dibenzoaceanthrylene (7a), 4H-fluorenoanthracene (8a), and 7H-dibenzofluorene (9a).The bridge ketone derivatives are most efficiently synthesized via treatment of the parent hydrocarbons with n-butyllithium and reaction of the resulting anionic intermediate s with molecular oxygen.The direct formation of ketones rather than the expected hydroperoxides from reaction of the bridge anions with O2 presumably involves intra- or intermolecular abstraction of a proton from the benzylic site of the intermediate by the peroxy anion leading to loss of hydroxide ion with formation of a carbonyl group.Yields are generally high except in the cases of 1a and 4a; the former affords as the principal product a dimeric alcohol arising from reaction of the anion of 1a with the corresponding ketone 1b.The related bridge alcohols are readily obtained in yields of 75-95percent by reduction of the crude products from the preceding oxidations with NaBH4.
Some Reactions on 4H-Cyclopentaphenanthrene-8,9-dione
Yoshida, Masaaki,Kadokura, Atsushi,Minabe, Masahiro,Suzuki, Kazuo
, p. 1179 - 1180 (2007/10/02)
The oxidation of 8,9-dihydro-4H-cyclopentaphenanthrene gave the 4-ketone by treatment with Triton B-oxygen, and afforded 8,9-diketone by the action of chromium (III) salt.The reduction of the quinone yielded the corresponding meso- and dl-diols.
