23683-68-3Relevant academic research and scientific papers
Synthesis and properties of oligonucleotides involving a perylene unit linked to a 2′-deoxyribose residue
Aubert, Yves,Asseline, Ulysse
, p. 1223 - 1225 (2003)
We report here the synthesis and binding properties of oligonucleotides involving a perylene unit linked to the anomeric position of a 2′-deoxyribose residue. Both anomers were separated and incorporated separately at either the 5′-end or the internal position of a pyrimidine sequence. In any case the presence of the perylene unit stabilizes the complexes formed with either the single or the double-stranded target.
Synthesis, photophysical and electrochemical properties of perylene dyes
Torres, érica,Berberan-Santos, Mário Nuno,Brites, Maria Jo?o
, p. 298 - 304 (2015)
Perylene dyes comprising: (i) 4-alkoxyphenylamino moiety in the 9-position as a strong donating group, (ii) cyanoacrylic acid as electron acceptor and anchoring group and (iii) a triple bond as short and rigid linker between perylene core and the acceptor group have been successfully synthesized. Their photophysical (i.e. absorption and emission spectra, molar extinction coefficients, fluorescence quantum yields and lifetime measurements) and electrochemical properties were investigated. The dyes display intense absorption in the visible exhibit high molar absorption coefficients making them good light harvesting materials for ss-DSCs.
Oxidative cyclodehydrogenation of a perylene derivative: different reagents give different products
Markoulides, Marios S.,Venturini, Chiara,Neumeyer, David,Gourdon, André
, p. 6498 - 6503 (2015)
An efficient synthesis of 3-fluoroterrylene, a promising molecular nanoprobe for single electron optical sensing, is described. The key synthetic steps comprised the palladium-catalysed cross-coupling reaction of 3-bromoperylene and 4-fluoronaphthalene-1-boronic acid pinacol ester to give 3-(4-fluoronaphthalen-1-yl)perylene, followed by oxidative cyclodehydrogenation to give selectively either 3-fluoroterrylene or its isomer 10-fluorobenzo[4,5]indeno[1,2,3-cd]perylene. The selectivity of the Scholl oxidation under AlCl3/chlorobenzene or DDQ/TfOH conditions was confirmed by 19F NMR.
Photooxygenation of alkynylperylenes. Formation of dibenzo[jk,mn] phenanthrene-4,5-diones
Maeda, Hajime,Nanai, Yasuaki,Mizuno, Kazuhiko,Chiba, Junya,Takeshima, Sakiko,Inouye, Masahiko
, p. 8990 - 8993 (2007)
(Chemical Equation Presented) 3-(1-Alkynyl)perylenes undergo oxygenation when subjected to irradiation with visible light under aerated conditions. The structures of novel oxygenated products formed in this manner are assigned as regioisomeric dibenzo[jk,
Communication of Bichromophore Emission upon Aggregation – Aroyl-S,N-ketene Acetals as Multifunctional Sensor Merocyanines
Biesen, Lukas,May, Lars,Nirmalananthan-Budau, Nithiya,Hoffmann, Katrin,Resch-Genger, Ute,Müller, Thomas J. J.
supporting information, p. 13426 - 13434 (2021/08/06)
Aroyl-S,N-ketene acetal-based bichromophores can be readily synthesized in a consecutive three-component synthesis in good to excellent yields by condensation of aroyl chlorides and an N-(p-bromobenzyl) 2-methyl benzothiazolium salt followed by a Suzuki coupling, yielding a library of 31 bichromophoric fluorophores with substitution pattern-tunable emission properties. Varying both chromophores enables different communication pathways between the chromophores, exploiting aggregation-induced emission (AIE) and energy transfer (ET) properties, and thus, furnishing aggregation-based fluorescence switches. Possible applications range from fluorometric analysis of alcoholic beverages to pH sensors.
Compound containing perylene and fluorobenzene as well as preparation method and application of compound
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Paragraph 0010; 0034-0037; 0044-0047; 0054-0057, (2021/01/21)
The invention discloses a compound containing perylene and fluorobenzene. The structure of the compound is shown as a formula 1, the preparation method of the compound comprises the following specificsteps: (1) reacting perylene with N-bromo succinimide to prepare a compound I; (2) reacting the compound I with bis (pinacolato) diboron to obtain a compound II; (3) reacting the compound II with 2,3, 5, 6-tetrafluoro-1, 4-dibromobenzene to prepare a compound III; and (4) reacting the compound III with pentafluorophenylboronic acid to obtain a compound IV. Based on good structural modification and various photoelectric properties of perylene and perylene series compounds, high-color-purity green-light LED devices can be prepared, and huge application potential in the aspect of green fluorescent powder for white-light LEDs is achieved.
Electron Push-Pull Effects on Intramolecular Charge Transfer in Perylene-Based Donor-Acceptor Compounds
Ahn, Mina,Kim, Min-Ji,Cho, Dae Won,Wee, Kyung-Ryang
, p. 403 - 413 (2020/12/23)
A series of asymmetric donor-acceptor (D-A) perylene-based compounds, 3-(N,N-bis(4′-(R)-phenyl)amino)perylene (Peri-DPA(R)), were successfully prepared to explore their intramolecular charge transfer (ICT) properties. To induce ICT between the donor and acceptor, diphenylamine (DPA) derivatives (electron donor units) with the same functional groups (R = CN, F, H, Me, or OMe) at both para positions were linked to the C-3 position of perylene to produce five Peri-DPA derivatives. A steady-state spectroscopy study on Peri-DPA(R)s exhibited a progressively regulated ICT trend consistent with the substituent effect as it progressed from the electron-withdrawing group to the electron-donating group. In particular, a comparative study using a D-A-D (donor-acceptor-donor) system demonstrated that not only the electron push-pull substituent effect but also subunit combinations influence photophysical and electrochemical properties. The different ICT characters observed in Lippert-Mataga plots of D-A(CN) and D-A-D(CN) (CN-substituted D-A and D-A-D) led to the investigation on whether ICT emission of two systems with differences in subunit combinations is of the same type or of a different type. The femtosecond transient absorption (fs-TA) spectroscopic results provided direct evidence of ICT origin and confirmed that D-A(CN) and D-A-D(CN) exhibited the same transition mix of ICT (from donor to acceptor) and reverse ICT (rICT, from arylamine to CN unit). Density functional theory (DFT)/TD-DFT calculations support the presence of ICT for all five compounds, and the experimental observations of rICT presented only for CN-substituted compounds.
Efficient Triplet–Triplet Annihilation Upconversion in Solution and Hydrogel Enabled by an S-T Absorption Os(II) Complex Dyad with an Elongated Triplet Lifetime
Wei, Yaxiong,Li, Yuanming,Li, Zefeng,Xu, Xinsheng,Cao, Xiaosong,Zhou, Xiaoguo,Yang, Chuluo
supporting information, p. 19001 - 19008 (2021/12/17)
A new Os(II) complex dyad featuring direct singlet-to-triplet (S-T) absorption and intramolecular triplet energy transfer (ITET) with lifetime up to 7.0 μs was designed to enhance triplet energy transfer efficiency during triplet–triplet annihilation upconversion (TTA-UC). By pairing with 9,10-bis(phenylethynyl)anthracene (BPEA) as a triplet acceptor, intense upconverted green emission in deaerated solution was observed with unprecedented TTA-UC emission efficiency up to 26.3% (with a theoretical maximum efficiency of 100%) under photoexcitation in the first biological transparency window (650–900 nm). Meanwhile, a 7.1% TTA-UC emission efficiency was acquired in an air-saturated hydrogel containing the photosensitizer and a newly designed hydrophilic BPEA derivative. This ITET mechanism would inspire further development of a highly efficient TTA-UC system for biological fields and renewable energy production.
Red or near-infrared light operating negative photochromism of a binaphthyl-bridged imidazole dimer
Kometani, Aya,Inagaki, Yuki,Mutoh, Katsuya,Abe, Jiro
, p. 7995 - 8005 (2020/05/27)
The development of red or near-infrared light (NIR) switchable photochromic molecules is required for an efficient utilization of sunlight and regulation of biological activities. While the photosensitization of photochromic molecules to red or NIR light has been achieved by a two-photon absorption process, the development of a molecule itself having sensitivity to red or NIR light has been now a challenging study. Herein, we developed an efficient molecular design for realizing red or NIR-light-responsive negative photochromism based on binaphthyl-bridged imidazole dimers. The introduction of electron-donating substituents shows the red shift of the absorption band at the visible-light region because of the contribution of a charge-transfer transition. Especially, the introduction of a di(4-methoxyphenyl)amino group (TPAOMe) and a perylenyl group largely shifts the absorption edge of the stable colored form to 900 nm. In addition, because the absorption band of one of the derivatives substituted with TPAOMe covers the whole visible-light region, the colored form shows a neutral gray color. Upon red (660 nm) or NIR-light (790 nm) irradiation, we observed the negative photochromic reaction from the stable colored form to the metastable colorless form. Therefore, the substituted binaphthyl-bridged imidazole dimers constitute the attractive photoswitches within a biological window.
Intersystem crossing: via charge recombination in a perylene-naphthalimide compact electron donor/acceptor dyad
Bussotti, Laura,Di Donato, Mariangela,Doria, Sandra,El-Zohry, Ahmed M.,Foggi, Paolo,Imran, Muhammad,Matt, Clemens,Mohammed, Omar F.,Taddei, Maria,Weber, Stefan,Zhao, Jianzhang
supporting information, p. 8305 - 8319 (2020/07/14)
In order to study the relationship between the molecular structures of compact electron donor/acceptor dyads and the spin-orbit charge transfer intersystem crossing (SOCT-ISC) efficiency, we prepared a perylene (Pery)-naphthalimide (NI) dyad, in which the Pery unit is the electron donor and the NI unit is the electron acceptor, where the two units adopt an almost orthogonal geometry. The photophysical properties of the dyad were studied with steady state and femtosecond/nanosecond transient absorption (fs TA and ns TA) spectroscopies, time resolved electron paramagnetic resonance (TREPR) spectroscopy and DFT computations. A very weak charge transfer (CT) absorption band was observed, but the fluorescence of the Pery unit is strongly quenched. Upon selective excitation into the NI unit, the fast intramolecular CS process (10 ps) occurs, followed by ISC and only the 3Pery? state is observed; whereas upon selective photoexcitation into the perylene unit, an ultrafast charge separation (0.66 ps) is observed, followed by SOCT-ISC (8 ns) to populate the 3Pery? state. Moreover, the perylene radical cation is also observed on the ns timescale, presumably formed by intermolecular charge transfer. The lifetime of the 3Pery triplet state was determined to be τT = 214 μs with ns TA spectroscopy. The singlet oxygen quantum yield was measured as ΦΔ = 80%, although the potential energy curve of the torsion between the donor and acceptor is shallow. The SOCT-ISC mechanism was confirmed by TREPR spectroscopy. The dyad was used as a triplet photosensitizer for the generation of delayed fluorescence (luminescence lifetime τDF = 57.3 μs). This journal is
