7149-49-7Relevant articles and documents
First-order hyperpolarizability of oligo-acene derivatives by hyper-Rayleigh scattering
Ishibashi, Kenichi,Iyoda, Tomokazu,Hashimoto, Kazuhito,Fujishima, Akira,Shirai, Yasuo,Jiro, Abe
, p. 107 - 111 (1997)
First-order hyperpolarizabilities β for a series of oligo-acene derivatives were estimated as a function of the conjugation length by means of the hyper-Rayleigh scattering (HRS) technique. Satisfactory data acquisition and analyses gave the hyperpolarizabilities (17 ± 2) × 10-30 and (68 ± 8) × 10-30 esu for naphthalene-2,3-dialdehyde and anthracene-2,3-dialdehyde, respectively. The pure β value of tetracene-2,3-dialdehyde (OA4) could not be determined because of multiphoton absorption induced fluorescence superimposed on the HRS signal. A large β value (≈ 180 × 10-30 esu) is expected for OA4 by extrapolating the conjugation length dependence on β.
A solvent-free mechanochemical synthesis of polyaromatic hydrocarbon derivatives
Wang, Cong,Hill, Malik,Theard, Brandon,MacK, James
, p. 27888 - 27891 (2019/09/30)
Polyaromatic hydrocarbons are central molecules in the future of nanotechnology. However, the synthesis of these molecules is limited by their lack of solubility in solvents, especially green solvents, their ease of oxidation in solution and use of harmful reagents. Solvent-free mechanochemistry has been shown to have excellent potential for these types of molecules and should provide a much more environmentally benign approach for the synthesis of this very important class of molecules. This report details the use of mechanochemistry on an iterative strategy for the synthesis of polyaromatic hydrocarbon derivatives.
Phosphine-Mediated Iterative Arene Homologation Using Allenes
Zhang, Kui,Cai, Lingchao,Jiang, Xing,Garcia-Garibay, Miguel A.,Kwon, Ohyun
, p. 11258 - 11261 (2015/09/21)
A PPh3-mediated multicomponent reaction between o-phthalaldehydes, nucleophiles, and monosubstituted allenes furnishes functionalized non-C2-symmetric naphthalenes in synthetically useful yields. When the o-phthalaldehydes were reacted with 1,3-disubstituted allenes in the presence of PPh2Et, naphthalene derivatives were also obtained in up to quantitative yields. The mechanism of the latter transformation is straightforward: aldol addition followed by Wittig olefination and dehydration. The mechanism of the former is a tandem γ-umpolung/aldol/Wittig/dehydration process, as established by preparation of putative reaction intermediates and mass spectrometric analysis. This transformation can be applied iteratively to prepare anthracenes and tetracenes using carboxylic acids as pronucleophiles.
Cycloadditions of siloxy alkynes with 1,2-diazines: From reaction discovery to identification of an antiglycolytic chemotype
Montavon, Timothy J.,Tuerkmen, Yunus E.,Shamsi, Noumaan A.,Miller, Christopher,Sumaria, Chintan S.,Rawal, Viresh H.,Kozmin, Sergey A.
supporting information, p. 13576 - 13579 (2014/01/06)
Cycloaddition uncovered: The title reaction produces novel polycyclic compounds with high efficiency and excellent diastereoselectivity under mild reaction conditions. A small-molecule library, synthesized using this reaction, yielded a novel chemotype which inhibited glycolytic ATP production by blocking glucose uptake in CHO-K1 cells. DMF=N,N-dimethylformamide, Tf= trifluoromethanesulfonyl, TIPS=triisopropylsilyl. Copyright
