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Theoretical study on intramolecular hydrogen transfer involving amino-substituted perylenequinone
Liu, W; Zhang, HY; Chen, DZ; Zhang, ZY; Zhang, MH
2000-12-01
Source PublicationDYES AND PIGMENTS
ISSN0143-7208
Volume47Issue:3Pages:277-284
Abstract2-Amino-perylenequinone (2-NH2-PQ) and 3,10-diamino-perylenequinone (3,10-diNH(2)-PQ) were used as model compounds for investigating the intramolecular hydrogen transfer (IHT) reactions involving amino-substituted perylenequinonoid photosensitizers (PQP). A semi-empirical MO method (AM1) was employed to calculate the theoretical values associated with the IHT process. It was found that amino-substitution enhanced the entropy of a specific isomer of PQ, causing it to be more stable than other possible isomers. Amino-substitution raised the HOMO energy levels (E-HOMO) Of PQ. by increasing its electron-donating ability. It was also found that placing an NH2 group in the 2-position lowered the energy barriers to IHT in PQ in the ground state and the singlet excited state, and 3,10-diNH(2)-substitution increased the ii-IT energy barriers in PQ in both states. The energy barrier for the double IHT was almost two times the energy barrier for the single IHT, making the double IHT a less important process. The II-IT energy barrier for NH2-PQ decreased in the singlet excited state, while the energy barrier decrease from the excited state to ground state was larger for 2-NH2-PQ than for 3,10-diNH(2)-PQ. The charge on the hydrogen atom and the molecular dipole moment varied during the Ii-IT process, and the IHT energy barriers were governed by the differences in the charges on the hydrogen atom in the transition state and initial state. The dipole moment for the molecular singlet excited st:lte changed considerably during the II-IT process, indicting that IHT would be accelerated by strongly polar solvents. Like the PQ case, there was no correlation between changes in the charge on the hydrogen atom and dipole moment changes in the IHT process. (C) 2000 Elsevier Science Ltd. All rights reserved.
KeywordAmi Method Amino-substituted Perylenequinonoid Photosensitizer Intramolecular Hydrogen Transfer Amino-substituted Perylenequinone Perylenequinonoid Photosensitizer
Indexed BySCI
Language英语
WOS IDWOS:000165486000008
PublisherELSEVIER SCI LTD
Citation statistics
Cited Times:6[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/76136
Collection中国科学院化学研究所
Corresponding AuthorZhang, HY
Affiliation1.Shandong Teachers Univ, Dept Biol, Jinan 250014, Peoples R China
2.Mengzi Teachers Inst, Yunnan Mengzi 661100, Peoples R China
3.Shandong Teachers Univ, Dept Chem, Jinan 250014, Peoples R China
4.Chinese Acad Sci, Inst Biophys, Beijing 100101, Peoples R China
5.Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100101, Peoples R China
Recommended Citation
GB/T 7714
Liu, W,Zhang, HY,Chen, DZ,et al. Theoretical study on intramolecular hydrogen transfer involving amino-substituted perylenequinone[J]. DYES AND PIGMENTS,2000,47(3):277-284.
APA Liu, W,Zhang, HY,Chen, DZ,Zhang, ZY,&Zhang, MH.(2000).Theoretical study on intramolecular hydrogen transfer involving amino-substituted perylenequinone.DYES AND PIGMENTS,47(3),277-284.
MLA Liu, W,et al."Theoretical study on intramolecular hydrogen transfer involving amino-substituted perylenequinone".DYES AND PIGMENTS 47.3(2000):277-284.
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