1714-29-0Relevant articles and documents
Effects of substituents on absorption and fluorescence properties of trimethylsilylethynyl- and tert-butylethynyl-pyrenes
Furuyama, Taniyuki,Maeda, Hajime,Segi, Masahito,Ueno, Ryota
, (2020)
Effects of substituents introduced at 1-position of trimethylsilylethynyl- and tert-butylethynyl-pyrenes on absorption and fluorescence properties were investigated. Fluorescence intensities of 1.0 × 10–5 M CH2Cl2 solutions of these pyrene derivatives were significantly larger than that of pyrene. Absorption of a silyl derivative having a formyl group shifted to longer wavelengths as the solvent polarity increased, whereas that of the carbon analog shifted to shorter wavelengths. On the other hand, in the solvent dependence of fluorescence, both fluorescence of them shifted to longer wavelengths as the polarity of the solvent increased. Fluorescence spectra of pyrene derivatives synthesized in this study at saturated concentrations in CH2Cl2 exhibited excimer emissions in the longer wavelength regions compared to that of unsubstituted pyrene. Fluorescence quantum yields of silicon analogs were higher than that of the corresponding carbon analogs in both solution and solid states. From the results of molecular orbital calculations, it was clarified that the effects of the substituents at the 1-position on the pyrene ring on the absorption and fluorescence properties can be explained by the properties of the molecular orbitals corresponding to the respective electron transitions.
Pyrene-Oxadiazoles for Organic Light-Emitting Diodes: Triplet to Singlet Energy Transfer and Role of Hole-Injection/Hole-Blocking Materials
Chidirala, Swetha,Ulla, Hidayath,Valaboju, Anusha,Kiran, M. Raveendra,Mohanty, Maneesha Esther,Satyanarayan,Umesh,Bhanuprakash, Kotamarthi,Rao, Vaidya Jayathirtha
, p. 603 - 614 (2016)
Three pyrene-oxadiazole derivatives were synthesized and characterized by optical, electrochemical, thermal, and theoretical investigations to obtain efficient multifunctional organic light emitting diode (OLED) materials. Synthesized molecules were used as emitters and electron transporters in three different device configurations, involving hole-injection/hole-blocking materials that showed good current and power efficiencies. To understand the underlying mechanisms involved in the application of these molecules as emitters and transporters, a detailed photophysical characterization of molecules 4-6 was carried out. The absorption, steady-state fluorescence, phosphorescence, fluorescence lifetime, and phosphorescence lifetime measurements were carried out. The high quantum yield and efficient reverse intersystem crossing leading to delayed fluorescence emission makes the molecule a good emitter, and the charge delocalization properties leading to excimer formation make them efficient electron transporters. Isoenergetic singlet and triplet states of the molecules make the reverse intersystem crossing feasible at room temperature even in the absence of thermal activation.
Novel ethynyl-pyrene substituted phenothiazine based metal free organic dyes in DSSC with 12% conversion efficiency
Nagarajan, Bhanumathi,Kushwaha, Suman,Elumalai, Ramachandran,Mandal, Sudip,Ramanujam, Kothandaraman,Raghavachari, Dhamodharan
, p. 10289 - 10300 (2017)
Six new dyes based on phenothiazine conjugated to an ethynyl-pyrene moiety are synthesized and characterized. Dye-sensitized solar cells are fabricated using these dyes with and without a co-adsorbent, chenodeoxychloicacid. Simple molecular engineering around the phenothiazine moiety enabled a maximum of 12% photoconversion efficiency with one of the dyes.
A mechanistically-distinct approach to fluorescence visualization of singlet oxygen
Yang,Finney
, p. 11449 - 11452 (2017)
We describe fluorescence detection of 1O2 by a new strategy. Oxidation of a non-fluorescent sulfoxide by 1O2 occurs via intramolecular oxygen atom transfer in a reactive persulfoxide intermediate. The resulting sulfone shows significantly enhanced (>50-fold) emission. This approach complements known methods, and is being extended to biological 1O2 imaging.
3-pyrenylacrylates: Synthetic, photophysical, theoretical and electrochemical investigations
Reimann, Sebastian,Sharif, Muhammad,Wittler, Kai,Knoepke, Leif R.,Surkus, Annette-E.,Roth, Christian,Ludwig, Ralf,Langer, Peter
, p. 367 - 377 (2013)
The Mizoroki-Heck coupling of 1-bromopyrene with acrylates provides a convenient access to a variety of 3-pyrenylacrylates in very good yields (up to 93%). Their photophysical properties combined with solvatochromic effects were studied. In addition, electrochemical oxidation potentials were determined by DPV (differential pulse voltammetry) measurements. The fine structure of the absorbance spectra obtained from photophysical measurements are compared with the results of theoretical calculations performed by time dependent TD-B3LYP methods using the 6-31G* basis set.
A pyrene-based dual chemosensor for colorimetric detection of Cu2+ and fluorescent detection of Fe3+
Guo, Yuxin,Wang, Lei,Zhuo, Jiezhen,Xu, Bo,Li, Xue,Zhang, Jianyu,Zhang, Zhiqiang,Chi, Haijun,Dong, Yan,Lu, Gonghao
, p. 3951 - 3956 (2017)
A pyrene based chemosensor was designed and synthesized. The pyrene fluorophore was connected with a pyridine unit through a Schiff base structure to give the sensor (L). L was tested with a variety of metal ions and exhibited high colorimetric selectivities for Cu2+ and Fe3+ over other ions. Upon binding with Cu2+ or Fe3+, L showed an obvious optical color change from colorless to pink for Cu2+ or orange for Fe3+ over a wide pH range from 3 to 12. Moreover, the fluorescence of L at 370 nm decreased sharply after bonding with Fe3+, while other metal ions including Cu2+ had no apparent interference. Thus, using such single chemosensor, Cu2+ and Fe3+ can be detected independently with high selectivity and sensitivity. The limits of detection toward Cu2+ and Fe3+ were 8.5 and 2.0 μM, respectively. DFT calculation results also proved the formation of stable coordination complexes and the phenomenon of fluorescence quenching by Fe3+. Furthermore, L was also successfully used as a bioimaging reagent for detection of Fe3+ in living cells.
Pyrene terminal functionalized perylene diimide as non-fullerene acceptors for bulk heterojunction solar cells
Liu, Xin,Luo, Guoping,Cai, Xinyi,Wu, Hongbin,Su, Shi-Jian,Cao, Yong
, p. 83155 - 83163 (2015)
Two perylene diimide (PDI) based small molecules with different terminal groups of pyrene and tert-butyl pyrene, namely P1 and P2, respectively, were designed and synthesized as the acceptor materials in organic solar cells (OSCs). The impacts of the different terminal groups combined with the PDI core on the optical absorption and fluorescence, electrochemical properties, film morphology, and solar cell performance were studied thoroughly. The two compounds possess a broad absorption covering the wavelength range of 400-650 nm and a relatively high LUMO energy level of 3.77 eV. Power conversion efficiency (PCE) of the OSCs based on P2 as the acceptor material and PTB7 as the donor material (1 : 1, w/w) is 0.41%. In contrast, a PCE of 1.35% was achieved for the device based on P1 as the acceptor and PTB7 as the donor (1 : 1, w/w).
Pseudo-dumbbell-type molecular beacon probes bearing modified deoxyuridine derivatives and a silylated pyrene as a fluorophore
Chowdhury, Jakir Ahmed,Moriguchi, Tomohisa,Shinozuka, Kazuo
, p. 496 - 502 (2015)
We have recently reported a novel pseudo-dumbbell-type molecular beacon probe (Probe 1) possessing polyamine-connected deoxyuridine (U) and silylated pyrene. The probe showed weak fluorescence signal while it stayed alone. Fluorescence signal of the probe was increased in the presence of the complementary DNA. In this study, we prepared new molecular beacons, Probe 2 and Probe 3, possessing the elongated stem portion of Probe 1. In addition, one U in Probe 2 is substituted by anthraquinone-bearing deoxyuridine residue (Y) in Probe 3. Probe 4 is essentially the same as Probe 1 but one deoxyguanosine in the loop portion of Probe 1 is substituted by deoxyinosine in Probe 4. In Probe 5, 3′- terminal deoxycytidine of Probe 3 is substituted by deoxyadenosine. The fluorescence signal of these probes is effectively quenched in the absence of target DNA. Among all, Probe 3 shows the most effective quenching. On the other hand, the signal is substantially increased in the presence of complementary DNA. The ratio of signal to background in case of Probe 3 is the highest. All these probes also recognize single nucleotide alternation in the target DNA to a different extent. The sequence recognition ability of Probe 3 is also the highest among all the probes.
The synthesis of polyarene-modified 5-phenyl-2,2'-bipyridines via the methodology and aza-Diels-Alder reaction
Kovalev, Igor S.,Kopchuk, Dmitry S.,Khasanov, Albert F.,Zyryanov, Grigory V.,Rusinov, Vladimir L.,Chupakhin, Oleg N.
, p. 117 - 118 (2014)
Nucleophilic substitution of hydrogen () in 6-phenyl-3-(2-pyridyl)-1,2,4- triazine under the action of lithium derivatives of polynuclear arenes followed by aza-Diels-Alder reaction with norbornadiene or morpholinocyclopentene gives the novel polyarenemodified photoluminescent 5-phenyl-2,2'-bipyridine ligands.
ON–OFF Fluorescent Imidazole Derivative for Sensitive and Selective Detection of Copper(II) Ions
Appalanaidu, E.,Baggi, T. R.,Harsha, K. G.,Rao, B. A.,Rao, V. J.
, p. 158 - 168 (2020)
A novel multichromophoric hybrid compound, 2-[1-(4-tert-butylphenyl)-4,5-diphenyl-1H-imidazol-2-yl]-6-(pyren-1-yl)quinoline (TDIPQ) has been synthesized as an ON-OFF fluorescent chemosensor for copper(II) ions. Colorless TDIPQ in acetonitrile—water (2:1, v/v) selectively turns yellow along with fluorescence quenching upon addition of copper(II) ions. The fluorescence quenching is directly proportional to the concentration of copper(II) ions. The interaction between TDIPQ and copper(II) was investigated with the aid of UV-Vis, fluorescence, 1H NMR, and MALDI mass spectral techniques. The stoichiometry of the TDIPQ—Cu complex was determined to be 2:1 by Job’s Plot. Under similar experimental conditions, other competitive metal ions had negligible or no interference in the detection ability of TDIPQ. The detection and quantification limits of TDIPQ were estimated at 2 × 10?6 M and 6.2 × 10?6 M. respectively. This method showed an excellent precision of 0.98 ± 0.011 and recovery characteristic of 99.09±1.4%. It is applicable for the quantification of copper(II) in various samples such as drinking water, lab waste water, and soil. A mixture of TDIPQ with the BZA-Co-BZMA polymer can be cast as a film on a glass slide to be used as a sensor device to indicate the presence of copper. Polymer-coated TDIPQ chemosensing property was analyzed by SEM imaging.
