Recently I am researching about PHOTOACTIVE YELLOW PROTEIN; CLUSTER-EXPANSION; EXCITED-STATES; WAVE-FUNCTION; ECTOTHIORHODOSPIRA-HALOPHILA; HYDRATED COMPLEX; METHYL CINNAMATE; SINAPIC ACID; DYNAMICS; SAC, Saw an article supported by the Institute for Quantum Chemical Exploration; JSPS KAKENHIMinistry of Education, Culture, Sports, Science and Technology, Japan (MEXT)Japan Society for the Promotion of ScienceGrants-in-Aid for Scientific Research (KAKENHI) [JP19K05387, 16H06511, 16H04104, JP16H04098, JP15KT0065]; Building of Consortia for the Development of Human Resources in Science and Technology, MEXT; JST, PRESTOJapan Science & Technology Agency (JST) [JPMJPR16N8]; JST, CRESTJapan Science & Technology Agency (JST)Core Research for Evolutional Science and Technology (CREST) [JPMJCR14L5]. Application In Synthesis of Methyl 3-phenyl-2-propenoate. Published in ROYAL SOC CHEMISTRY in CAMBRIDGE ,Authors: Kinoshita, S; Inokuchi, Y; Onitsuka, Y; Kohguchi, H; Akai, N; Shiraogawa, T; Ehara, M; Yamazaki, K; Harabuchi, Y; Maeda, S; Ebata, T. The CAS is 103-26-4. Through research, I have a further understanding and discovery of Methyl 3-phenyl-2-propenoate
The electronic states and photochemistry including nonradiative decay (NRD) and trans(E) -> cis(Z) isomerization of methylcinnamate (MC) and its hydrogen-bonded complex with methanol have been investigated under jet-cooled conditions. S-1((1)n pi*) and S-2((1)pi pi*) are directly observed in MC. This is the first direct observation of S-1(1n pi*) in cinnamate derivatives. Surprisingly, the order of the energies between the n pi* and pi pi* states is opposite to substituted cinnamates. TD-DFT and SAC-CI calculations support the observed result and show that the substitution to the benzene ring largely lowers the (1)pi pi* energy while the effect on (1)n pi* is rather small. The S-2(pi pi*) state lifetime of MC is determined to be equal to or shorter than 10 ps, and the production of the transient T-1 state is observed. The T-1(pi pi*) state is calculated to have a structure in which propenyl C=C is twisted by 90 degrees, suggesting the trans -> cis isomerization proceeds via T-1. The production of the cis isomer is confirmed by low-temperature matrix-isolated FTIR spectroscopy. The effect of H-bonding is examined for the MC-methanol complex. The S-2 lifetime of MC-methanol is determined to be 180 ps, indicating that the H-bonding to the C=O group largely prohibits the (1)pi pi* -> (1)n pi* internal conversion. This lifetime elongation in the methanol complex also describes well a higher fluorescence quantum yield of MC in methanol solution than in cyclohexane, while such a solvent dependence is not observed in para-substituted MC. Determination of the photochemical reaction pathways of MC and MC-methanol will help us to design photofunctional cinnamate derivatives.
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Reference:
Article; Weng, Shiue-Shien; Ke, Chih-Shueh; Chen, Fong-Kuang; Lyu, You-Fu; Lin, Guan-Ying; Tetrahedron; vol. 67; 9; (2011); p. 1640 – 1648;,
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