7415-79-4Relevant academic research and scientific papers
Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources
Zullo, Valerio,Iuliano, Anna,Pescitelli, Gennaro,Zinna, Francesco
supporting information, (2022/02/19)
Organic compounds showing circularly polarized luminescence (CPL) are at the forefront of novel applications and technologies. Here we show the synthesis and chiroptical properties of pyrene and perylene derivatives of inexpensive chiral scaffolds: isomannide and isosorbide. Low-intensity ECD spectra were obtained, suggesting the absence of chromophore interaction in the ground state, except in the case of isomannide bis-perylenecarboxylate, whose ECD spectrum showed a positive exciton couplet. All isomannide derivatives, with the only exception of the one containing a pyrenecarboxylate and a perylenecarboxylate, exhibited excimer CPL spectra, whereas isosorbide derivatives did not show any CPL. Isomannide derivatives bearing two pyrenecarboxylate or two pyrenylacetate groups showed positive CPL emission with dissymmetry factors up to 10?2, which depends on the conformational freedom of the appended units. The CPL sign, Stokes shift and order of magnitude of dissymmetry factor were reproduced by excited-state calculations on a representative compound. Interestingly, the mixed derivative containing pyrenic units with different spacing from the isomannide scaffold showed an oppositely signed excimer band with respect to the homo-substituted derivatives.
2-Ethynylperylene and improved synthesis of 3-ethynylperylene
Chistov, Alexey A.,Kutyakov, Sergey V.,Ustinov, Alexey V.,Aparin, Ilya O.,Glybin, Anton V.,Mikhura, Irina V.,Korshun, Vladimir A.
supporting information, p. 1003 - 1005 (2016/02/18)
3-Ethynylperylene 1, an important precursor for fluorescent dyes, fluorescent nucleosides, and potent nucleoside-based antivirals, has been prepared from perylene on a multigram scale (3 steps, 55% overall yield). A simple synthesis of 2-ethynylperylene 2 from perylene (5 steps, 20% yield) has been developed. UV and fluorescence spectra of the ethynylperylenes 1 and 2 are compared to those of perylene.
Photoinduced symmetry-breaking charge separation: The direction of the charge transfer
Markovic, Vesna,Villamaina, Diego,Barabanov, Igor,Lawson Daku, Latevi Max,Vauthey, Eric
supporting information; experimental part, p. 7596 - 7598 (2011/10/01)
Even flow: Photoinduced symmetry-breaking charge separation takes place in a few picoseconds in a 1,3-bis(perylene)propane dyad in polar solvents. Polarized transient absorption measurements show that the direction of the charge flow is random and entirely governed by the fluctuations of the solvent orientation around the dyad. Copyright
Superacid-catalyzed dimerization/cyclization of isopropenyl-PAHs - Novel pathways to PAH dimers, phenalenes and their stable carbocations
Brule, Cedric,Sultana, Fatima,Hollenstein, Sandro,Okazaki, Takao,Laali, Kenneth K.
experimental part, p. 3700 - 3708 (2009/04/11)
The isopropenyl derivatives of representative classes of polycyclic aromatic hydrocarbons (PAHs) having four and five fused-ring systems, namely pyrene, chrysene, benzo[c]phenanthrene (BcPh), dibenzo[a,c]anthracene (benzo[f]tetraphene) and perylene, were synthesized by Wittig olefination from the corresponding acetyl-PAHs. Under the influence of triflic acid (TfOH), the isopropenyl derivatives were converted to novel PAH dimers and/or phenalenes in a simple one-pot procedure. A plausible mechanism for this process has been outlined, and the synthetic scope of this chemistry has been explored. Structural features in the PAH dimers were examined by DFT. As representative initial and final carbocation intermediates in the reaction sequence, stable carbocations derived from 3-isopropenylperylene and from 4,6,6-trimethyl-6H- dibenzo[a,kl]anthracene were generated and studied directly by NMR spectroscopy. The NMR characteristics and charge delocalization modes in the resulting benzylic carbocations are discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Intelligent fluorescent nucleoside in sensing cytosine base: Importance of hydrophobic nature of perylene fluorophore
Bag, Subhendu Sekhar,Saito, Yoshio,Hanawa, Kazuo,Kodate, Satoshi,Suzuka, Isamu,Saito, Isao
, p. 6338 - 6341 (2007/10/03)
Fluorescence response upon hybridization of perylene labeled oligonucleotide probes depends on the microenvironment experienced by the perylene fluorophore. In mismatched duplex (PerU-C), enhanced fluorescence was observed while in matched dupl
Flash vacuum thermolysis of acenaphtho[1,2-a]acenaphthylene, fluoranthene, benzo[k]- and benzo[j]fluoranthene - Homolytic scission of carbon-carbon single bonds of internally fused cyclopenta moieties at T ≥ 1100°C
Sarobe, Martin,Kwint, Huibert C.,Fleer, Theun,Havenith, Remco W.A.,Jenneskens, Leonardas W.,Vlietstra, Edward J.,Van Lenthe, Joop H.,Wesseling, Jolanda
, p. 1191 - 1200 (2007/10/03)
Flash vacuum thermolysis (FVT, 1000 °C ≥ T ≥ 1200 °C) of acenaphtho[1,2-a]acenaphthylene (3, C22H12) gave the C22H12 cyclopenta-fused polycyclic aromatic hydrocarbon (CP-PAH) acenaphtho[1,2- e]acenaphthylene (4), cyclopenta[cd]perylene (5) and cyclopenta[def]benzo[hi]chrysene (6). Whereas the formation of 4 is explained by a ring contraction/ring expansion rearrangement of 3, the identification of 5 and 6 suggests that 3 also undergoes homolytic scission of a five- membered ring's carbon-carbon single bond furnishing the transient diradical intermediate 7. Ring closure of 7 to form 8 after rotation around the carbon- carbon single bond of the intact five-membered ring followed by hydrogen shifts will give 6. The latter can rearrange subsequently into 5 by ring contraction/ring expansion. The structural assignment of 4 and 5 was supported by independent FVT of 6,12-bis(1-chloroethenyl)chrysene (14) and 3- (1-chloroethenyl)perylene (23), respectively. FVT of 14 (900-1200 °C) gave in a consecutive process 6,12-bis(ethynyl)chrysene (15), 9- ethynylbenz[j]acephenanthrylene (16) and bis(cyclopenta[hi,qr])chrysene (17). Although at T ≥ 900 °C 17 selectively rearranges into 4 by ring contraction/ring expansion, at 1200 °C the latter is converted into 5 presumably via a diradical intermediate obtained by homolytic scission of a single carbon-carbon bond of a five-membered ring. FVT of 23 gave in situ 3- ethynylperylene (25), which at 1000 °C is nearly quantitatively converted into 5. The propensity of internal cyclopenta moieties to undergo homolytic scission of a five-membered ring's carbon-carbon single bond was corroborated by independent FVT of benzo[k]- (11) and benzo[j]fluoranthene (12). Previously unknown thermal pathways to important (CP)-PAH combustion effluents are disclosed at T≥ 1000 °C.
New fluorescent nucleoside derivatives - 5-alkynylated 2'-deoxyuridines
Korshun,Manasova,Balakin,Malakhov,Perepelov,Sokolova,Berlin
, p. 1809 - 1812 (2007/10/03)
Four fluorescent nucleosides, 5-(4-pyrenylethynyl)-, 5-(1- pyrenylbutadiynyl)-, 5-(3-perylenylethynyl)-, and 5-[4-(2- benzoxazolyl)phenylethynyl]-2'deoxyuridines, were synthesized.
