13752-40-4Relevant academic research and scientific papers
Synthesis and reactivity of anthracenyl-substituted arenediynes
Nagarjuna, Gavvalapalli,Ren, Yi,Moore, Jeffrey S.
, p. 3155 - 3159 (2015)
Cyclization reaction pathways of aryl-substituted arenediynes depend on the interplay between the steric interactions and electronic properties of the aryl substituents. Herein, to further probe the impact of bulky and electron rich aryl substituents on t
Dynamics of the formation of a charge transfer state in 1,2-bis(9-anthryl)acetylene in polar solvents: Symmetry reduction with the participation of an intramolecular torsional coordinate
Gutieì?rrez-Arzaluz, Luis,Guarin, Cesar A.,Rodriì?guez-Coì?rdoba, William,Peon, Jorge
, p. 12175 - 12183 (2013)
We have studied 1,2-bis(9-anthryl)acetylene as a model compound for the characterization of the process of solvent-mediated symmetry reduction in an excited state. Thanks to the acetylenic bridge that joins the two anthracenic moieties, this system maintains minimal steric hindrance between the end chromophores in comparison with the classic 9,9a?2-bianthryl model compound. The acetylenic bridge also allows for significant electronic coupling across the molecule, which permits a redistribution of electron density after light absorption. Femtosecond resolved fluorescence measurements were used to determine the spectral evolution in acetonitrile and cyclohexane solutions. We observed that, for 1,2-bis(9-anthryl)acetylene, the formation of a charge transfer state occurs in a clear bimodal fashion with well separated time scales. Specifically, the evolution of the emission spectrum involves a first solvent-response mediated subpicosecond stage where the fluorescence changes from that typical of nonpolar solvents (locally excited) to an intermediate, partial charge transfer state. The second stage of the evolution into a full charge transfer state occurs with a much longer time constant of 37.3 ps. Since in this system the steric hindrance is minimized, this molecule can undergo much larger amplitude motions for the torsion between the two anthracenic moieties associated with the charge redistribution in comparison with the typical model compound 9,9a?2-bianthryl. Clearly, the larger range of motions of 1,2-bis(9-anthryl)acetylene gives the opportunity to study the electron transfer process with a good separation of the time scales for the formation of a partial charge transfer state, determined by the speed of solvent response, and the intramolecular changes associated with the formation of the fully equilibrated charge transfer state. ? 2013 American Chemical Society.
Light-driven reversible surface functionalization with anthracenes: visible light writing and mild UV erasing
Claus, Tanja K.,Telitel, Siham,Welle, Alexander,Bastmeyer, Martin,Vogt, Andrew P.,Delaittre, Guillaume,Barner-Kowollik, Christopher
, p. 1599 - 1602 (2017)
We introduce a methodology to reversibly pattern planar surfaces via the light-induced dimerization of anthracenes, particularly involving a 9-triazolylanthracene motif. Specifically, we demonstrate that the visible light-induced forward reaction can be employed to pattern small molecule species as well as polymers in a spatially resolved fashion. Under UV irradiation, the generated patterns can be erased to regenerate reactive areas, which are then available for a new functionalization step. The dynamic change in surface chemistry is evidenced by ToF-SIMS.
Photoinduced Electron-Transfer-Based Hybridization Probes for Detection of DNA and RNA
Takahashi, Kan,Ito, Shun,Nakamoto, Kosuke,Ito, Yasutomo,Ueno, Yoshihito
, p. 8561 - 8570 (2015)
Here, we report the synthesis of a hybridization probe for detection of RNA and DNA based on photoinduced electron transfer (PeT). We designed and synthesized an oligonucleotide containing an adenosine analogue with a 9-(N,N-dimethylaminomethyl)anthraceny
Facile preparation and investigation of the properties of single molecular POSS-based white-light-emitting hybrid materials using click chemistry
Zhao, Gang,Zhu, Yakun,Guang, Shanyi,Ke, Fuyou,Xu, Hongyao
, p. 555 - 563 (2018)
Recently, organic white light emitting devices (OWLEDs) have attracted great interest in flexible displays and solid state lighting devices. Here we report a kind of novel POSS-based white-light-emitting single molecular nanohybrid (POSS-WLED), which was
Novel, yellow-emitting anthracene/fluorene oligomers: synthesis and characterization
Zhao, Zujin,Yu, Shuqiang,Xu, Lei,Wang, Hongbo,Lu, Ping
, p. 7809 - 7815 (2007)
A novel series of highly soluble and strongly yellow fluorescent with well-controlled, alternative anthracene, and fluorene units were successfully synthesized by a Pd/Cu-catalyzed Sonogashira coupling reaction and characterized. Their thermal stabilities
Tris(trifluoromethyl)germylethynyl derivatives of biphenyl and anthracene: Synthesis, structure, and evidence of the intramolecular charge transfer on the germanium center
Ermolaev, Nikolai L.,Lenin, Ilya V.,Fukin, Georgii K.,Shavyrin, Andrei S.,Lopatin, Mikhail A.,Kuznetsova, Olga V.,Andreev, Boris A.,Kryzhkov, Denis I.,Ignatov, Stanislav K.,Chuhmanov, Evgeny P.,Berberova, Nadezhda T.,Pashchenko, Konstantin P.
, p. 83 - 95 (2015)
Symmetrical and unsymmetrical 4,4′-biphenyl, and 9,10-anthracene derivatives with tris(trifluoromethyl)germylethynyl -CC-Ge(CF3)3 substitutes have been prepared, their properties have been studied and compared with those of dimethyl(
Manipulation of Foerster energy transfer of coupled fluorophores through biotransformation by Pseudomonas resinovorans CA10
Daniele, Michael A.,Bandera, Yuriy P.,Foulger, Stephen H.
, p. 129 - 134 (2012)
An alkyne-terminated anthracene and azide-terminated carbazole were joined through a copper-catalyzed cycloaddition to form a joined donor/acceptor pair. The photonic pair exhibited energy transfer when excited at the peak absorbance of carbazole and fluoresced with an anthracene spectral response. The fluorescent behavior was confirmed as Foerster energy transfer (FRET). The lysate of Pseudomonas resinovorans CA10, a member of a predominant group of soil microorganisms that can metabolize a host of substrates, was employed to degrade the pair and alter the luminance spectral characteristics. The FRET was diminished and the corresponding, individual fluorescence of carbazole and anthracene returned. This general approach may find applications in single-cell metabolic studies and bioactivity assays. 2011 Wiley Periodicals, Inc. Photochemistry and Photobiology
Alkyl Chain Length-Selective Vapor-Induced Fluorochromism of Pillar[5]arene-Based Nonporous Adaptive Crystals
Li, Qi,Zhu, Huangtianzhi,Huang, Feihe
, p. 13290 - 13294 (2019)
Developing new vapochromic fluorescent sensing materials with selectivity is in great demand due to serious air pollution caused by volatile organic compounds. Here we report the first nonporous adaptive crystals with vapor-induced fluorochromism. The emission of anthracene conjugated pillar[5]arene P5en crystals blue shifts from bright yellow to green upon exposure to vapors of linear alkyl ketones with alkyl chain length selectivity. Powder and single crystal X-ray diffraction analyses reveal the relationship between vapor-induced crystal structural transformation and fluorochromism. After exposure to 2-butanone, 2-pentanone, and 2-hexanone, the anthracene groups in P5en exist as monomers in the solid state, while after exposure to heptanone and octanone, the anthracene groups instead aggregate as excimers in the solid state. By solid-state NMR and thermogravimetric analysis, we further find that the size fit between ketone molecules and interspaces in P5en crystals lead to the alkyl chain length selectivity. This work provides a new strategy to design vapochromic fluorescent crystalline materials and crystalline transformation systems.
Multicolor Mechanofluorophores for the Quantitative Detection of Covalent Bond Scission in Polymers
Baumann, Christoph,Centeno, Silvia P.,G?stl, Robert,Stratigaki, Maria
, p. 13287 - 13293 (2021)
The fracture of polymer materials is a multiscale process starting with the scission of a single molecular bond advancing to a site of failure within the bulk. Quantifying the bonds broken during this process remains a big challenge yet would help to understand the distribution and dissipation of macroscopic mechanical energy. We here show the design and synthesis of fluorogenic molecular optical force probes (mechanofluorophores) covering the entire visible spectrum in both absorption and emission. Their dual fluorescent character allows to track non-broken and broken bonds in dissolved and bulk polymers by fluorescence spectroscopy and microscopy. Importantly, we develop an approach to determine the absolute number and relative fraction of intact and cleaved bonds with high local resolution. We anticipate that our mechanofluorophores in combination with our quantification methodology will allow to quantitatively describe fracture processes in materials ranging from soft hydrogels to high-performance polymers.
