20589-63-3Relevant articles and documents
The effects of 1-and 3-positions substitutions on the photophysical properties of perylene and its application in thiol fluorescent probes
Chen, Xiaoping,Dong, Fangdi,He, Huahong,He, Qin,Huo, Yanping,Ji, Shaomin,Wang, Huaqian,Xing, Longjiang
, (2021/12/02)
A series of perylene derivatives bearing electron-donating group (amino) and electron-withdrawing group (nitro, maleimide) at the 1- and 3-position have been synthesized. Interestingly, 3-monosubstituted perylenes shown different photophysical properties compared with 1-monosubstituted perylenes. 3-nitroperylene (3-NO) attained 80.62% photoluminescence quantum yield (ΦPL) in toluene which is higher than 3-aminoperylene (3-NH, ΦPL = 71.70%) and 1-aminoperylene (1-NH, ΦPL = 48.04%), but for 1-nitroperylene (1-NO), no fluorescence in any solvent were observed. The calculated ground-state geometries of 3-monosubstituted perylenes actually correspond to nearly planar structures, but the molecules substituted at the 1-position all have a twisted structure. Among them, 3-NO had a great π-conjugated system, resulting in the allowed ππ? fluorescence. In contrast, the twisting structure of 1-NO enhanced nonradiative decay pathways, coupled with the electron-withdrawing effect of the nitro group, which can explain the non-luminescence of 1-NO. Furthermore, the moleculars with maleimide group were used as “off-on” fluorescent probes and successfully used for imaging biothiols in living H1299 lung cancer cells. The fluorescence of probe 2 (substitutes at 3-position of perylene) afforded a 188-fold intensity increase after reaction with thiol which is much higher than (65-fold) probe 1 (substitutes at 1-position) because of the better π-conjugated structure. We envision that the investigation on the effects of substitute at 1-and 3-positions of perylene may be helpful for a rational design and application of highly fluorescent molecule base on perylene.
PHENANTHRO[1,10,9,8-C,D,E,F,G]CARBAZOLE POLYMERS AND THEIR USE AS ORGANIC SEMICONDUCTORS
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Page/Page column 43, (2011/02/24)
The invention relates to novel phenanthro[1,10,9,8-c,d,e,f,g]carbazole polymers, methods and materials for their preparation, their use as semiconductors in organic electronic (OE) devices, and to OE devices comprising these polymers.
Abnormal orientation in nitration of anthracene, pyrene, and perylene with pyridinium nitrate. 2-Nitroanthracene and 4-nitropyrene
Nefedov
, p. 1165 - 1171 (2007/10/03)
Nitration by undissociated nitric acid which presumably forms at thermolysis (115°C) of pyridinium nitrate in pyridine selectively proceeds with respect to aromatic substrates and nonselectively with respect to various positions in aromatic rings. Whereas in electrophilic nitration forms a single isomer of mononitro products, the process under study yields two mononitro isomers, and nitration occurs only with polycyclic hydrocarbons containing a butadiene fragment included into neighboring rings (anthracene, naphthacene, pyrene, and perylene). On the contrary, benzene and its derivatives, naphthalene, phenanthrene, and triphenylene are not nitrated. Beside pyridinium nitrate as nitrating agents giving two isomeric mononitro arenes from polycyclic compounds are used tetranitromethane in pyridine and ammonium nitrate in a mixture pyridine-acetic anhydride. The side products of the reaction are biaryls, quinones (in particular, with unusually located carbonyl groups), and dyes containing aci-nitro and oxo groups.