525-82-6Relevant articles and documents
Chapter Open for the Excited-State Intramolecular Thiol Proton Transfer in the Room-Temperature Solution
Chang, Chao-Che,Chen, Chao-Tsen,Chou, Pi-Tai,Huang, Chun-Hao,Li, Elise Y.,Liao, Yu-Chan,Liu, Yi-Hung,Liu, Zong-Ying,Meng, Fan-Yi,Wang, Chun-Hsiang
supporting information, p. 12715 - 12724 (2021/08/30)
We report here, for the first time, the experimental observation on the excited-state intramolecular proton transfer (ESIPT) reaction of the thiol proton in room-temperature solution. This phenomenon is demonstrated by a derivative of 3-thiolflavone (3TF), namely, 2-(4-(diethylamino)phenyl)-3-mercapto-4H-chromen-4-one (3NTF), which possesses an - S - H···O= intramolecular H-bond (denoted by the dashed line) and has an S1 absorption at 383 nm. Upon photoexcitation, 3NTF exhibits a distinctly red emission maximized at 710 nm in cyclohexane with an anomalously large Stokes shift of 12 230 cm-1. Upon methylation on the thiol group, 3MeNTF, lacking the thiol proton, exhibits a normal Stokes-shifted emission at 472 nm. These, in combination with the computational approaches, lead to the conclusion of thiol-type ESIPT unambiguously. Further time-resolved study renders an unresolvable (180 fs) ESIPT rate for 3NTF, followed by a tautomer emission lifetime of 120 ps. In sharp contrast to 3NTF, both 3TF and 3-mercapto-2-(4-(trifluoromethyl)phenyl)-4H-chromen-4-one (3FTF) are non-emissive. Detailed computational approaches indicate that all studied thiols undergo thermally favorable ESIPT. However, once forming the proton-transferred tautomer, the lone-pair electrons on the sulfur atom brings non-negligible nπ? contribution to the S1′ state (prime indicates the proton-transferred tautomer), for which the relaxation is dominated by the non-radiative deactivation. For 3NTF, the extension of π-electron delocalization by the diethylamino electron-donating group endows the S1′ state primarily in the ππ? configuration, exhibiting the prominent tautomer emission. The results open a new chapter in the field of ESIPT, covering the non-canonical sulfur intramolecular H-bond and its associated ESIPT at ambient temperature.
A novel one-pot synthesis of flavones
Chang, Meng-Yang,Tsai, Min-Chen,Lin, Chun-Yi
, p. 11655 - 11662 (2021/03/31)
In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.
METHOD FOR SYNTHESIZING (Z)-AURONE AND DERIVATIVE COMPOUNDS THEREOF
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Paragraph 0134-0135; 0140, (2021/05/11)
One embodiment of the present invention is described below. Provided is (Z)-operon comprising o - (alkanone -1 - yl) phenol or its derivative compound in a thallium (Tl) catalyst and an cyclization step for cyclizing the compound under an organic solvent, and a method for producing the derivative compound.