78053-62-0Relevant academic research and scientific papers
1,8-Bis(phenylethynyl)anthracene-gas and solid phase structures
Lamm, Jan-Hendrik,Horstmann, Jan,Stammler, Hans-Georg,Mitzel, Norbert W.,Zhabanov, Yuriy A.,Tverdova, Natalya V.,Otlyotov, Arseniy A.,Giricheva, Nina I.,Girichev, Georgiy V.
, p. 8893 - 8905 (2015/08/24)
1,8-Bis(phenylethynyl)anthracene (1,8-BPEA) was synthesized by a twofold Kumada cross-coupling reaction. The molecular structure of 1,8-BPEA was determined using a combination of gas-phase electron diffraction (GED), mass spectrometry (MS), quantum chemic
Photoactivatable anthracenes
Thapaliya, Ek Raj,Captain, Burjor,Raymo, Francisco M.
, p. 3973 - 3981 (2014/05/20)
Fifteen substituted maleimide cycloadducts of anthracene derivatives were synthesized in one or two steps from available precursors in yields ranging from 32 to 63%. They differ in the nature of the group on the maleimide nitrogen atom and of the substituents on the anthracene platform. In all instances, the introduction of a maleimide bridge across positions 9 and 10 of the anthracene skeleton isolates electronically its peripheral phenylene rings and suppresses its characteristic fluorescence. The cycloadducts with a 4-(dimethylamino)phenyl group on the maleimide nitrogen atom undergo retro-cycloaddition upon ultraviolet illumination with quantum yields ranging from 0.001 to 0.01. This structural transformation restores the aromatic character of the central ring of the oligoacene chromophore and activates its emission with fluorescence quantum yields ranging from 0.07 to 0.85. Thus, this particular choice of building blocks for the construction of photoresponsive compounds can translate into viable operating principles for fluorescence activation and, ultimately, lead to the realization of valuable photoactivatable fluorophores for imaging applications.
Autocatalytic fluorescence photoactivation
Thapaliya, Ek Raj,Swaminathan, Subramani,Captain, Burjor,Raymo, Franisco M.
supporting information, p. 13798 - 13804 (2015/02/18)
We designed an autocatalytic photochemical reaction based on the photoinduced cleavage of an α-diketone bridge from the central phenylene ring of a fluorescent anthracene derivative. The product of this photochemical transformation sensitizes its own formation from the reactant, under illumination at a wavelength capable of exciting both species. Specifically, the initial and direct excitation of the reactant generates the product in the ground state. The subsequent excitation of the latter species results in the transfer of energy to another molecule of the former to establish an autocatalytic loop. Comparison of the behavior of this photoactivatable fluorophore with that of a model system and the influence of dilution on the reaction progress demonstrates that the spectral overlap between the emission of the product and the absorption of the reactant together with their physical separation govern autocatalysis. Indeed, both parameters control the efficiency of the resonant transfer of energy that is responsible for establishing the autocatalytic loop. Furthermore, the proximity of silver nanoparticles to reactant and product increases the energy-transfer efficiency with a concomitant acceleration of the autocatalytic process. Thus, this particular mechanism to establish sensitization offers the opportunity to exploit the plasmonic effects associated with metallic nanostructures to boost photochemical autocatalysis.
Improved synthesis of 1,8-diiodoanthracene and its application to the synthesis of multiple phenylethynyl-substituted anthracenes
Goichi, Michio,Segawa, Kazushi,Suzuki, Shinya,Toyota, Shinji
, p. 2116 - 2118 (2007/10/03)
1,8-Diiodoanthracene was synthesized from 1,8-dichloroanthraquinone in three steps by improved procedures in 41% overall yield. Some anthracene derivatives carrying multiple phenylethynyl groups were synthesized from 1,8-diiodoanthracene and 4,5-diiodo-9-
