753006-66-5Relevant academic research and scientific papers
Quantum-chemical analysis of the Algar-Flynn-Oyamada reaction mechanism
Serdiuk,Roshal,B?a?ejowski
, p. 396 - 403 (2014/08/05)
This work is devoted to improving the understanding of Algar-Flynn-Oyamada reaction mechanism and the analysis of factors that affect the formation of flavonols. The calculation of thermodynamic parameters for the key reaction steps pointed to a mechanism involving chalcone epoxides as intermediates. A correlation was identified between the nucleophilicity of oxygen atom at position 2' of epoxide anions and the yields of flavonols. An increased charge at the nucleophilic center was shown to reduce the effectiveness of β-cyclization of epoxide anions.
Tuning excited-state charge/proton transfer coupled reaction via the dipolar functionality
Chou, Pi-Tai,Huang, Chien-Huang,Pu, Shih-Chieh,Cheng, Yi-Ming,Liu, Yi-Hong,Wang, Yu,Chen, Chao-Tsen
, p. 6452 - 6454 (2008/01/27)
Based on design and synthesis of I, II, and III, we demonstrate an ingenious approach to fine-tuning the excited-state intramolecular charge transfer (ESICT) coupled excited-state intramolecular proton transfer (ESIPT) reaction via the dipolar functionality of the molecular framework. Both I and II exhibit remarkable dual emission due to the different solvent-polarity environment between ESICT and ESIPT states, while the interplay of two charge-transfer entities in III leads to ESIPT decoupling from the solvent-polarity effect, resulting in a unique proton-transfer tautomer emission. The results make further rational design of the ESICT/ESIPT coupled systems feasible simply by tuning the net dipolar effect. Accordingly, systematic investigation of the correlation in regards to the difference in dipolar vectors between ESICT and ESIPT versus solvent-polarity induced barriers becomes possible.
