赖氨酸衍生物含两个三苯胺基荧光团的光物理和光化学特性

IF 2.8 2区 化学 Q3 CHEMISTRY, PHYSICAL
Mario Saletti, Marco Paolino, Jacopo Venditti, Gianluca Giorgi, Claudia Bonechi, Alessandro Donati, Claudio Rossi, Germano Giuliani, Antonella Caterina Boccia, Chiara Botta, Lluís Blancafort and Andrea Cappelli*, 
{"title":"赖氨酸衍生物含两个三苯胺基荧光团的光物理和光化学特性","authors":"Mario Saletti,&nbsp;Marco Paolino,&nbsp;Jacopo Venditti,&nbsp;Gianluca Giorgi,&nbsp;Claudia Bonechi,&nbsp;Alessandro Donati,&nbsp;Claudio Rossi,&nbsp;Germano Giuliani,&nbsp;Antonella Caterina Boccia,&nbsp;Chiara Botta,&nbsp;Lluís Blancafort and Andrea Cappelli*,&nbsp;","doi":"10.1021/acs.jpcb.5c0103210.1021/acs.jpcb.5c01032","DOIUrl":null,"url":null,"abstract":"<p >A Morita–Baylis–Hillman adduct (MBHA) derivative bearing a triphenylamine (TPA) moiety was previously found to react with Nα-acetyl-<span>l</span><i>-</i>lysine methyl ester with the formation of the corresponding diadduct derivative as the major reaction product and a monoadduct as the minor one. The characterization of photochemical features of the diadduct bearing two triphenylaminocinnamic (TPAC) fluorophores suggested that this compound shows the tendency to undergo the [2 + 2] photocycloaddition reaction. This hypothesis was evaluated in the present study in both the diadduct derivatives obtained with Nα-acetyl-<span>l</span>-lysine methyl ester and Nα-acetyl-<span>l</span>-lysine. The hypothesis was confirmed in the case of the diadduct derivative obtained from Nα-acetyl-<span>l</span>-lysine methyl ester, whereas the UV-A irradiation of the diadduct derivative obtained from Nα-acetyl-<span>l</span>-lysine led to the formation of a strongly emissive (QY = 69%, λ<sub>em</sub> = 460 nm) symmetric dimer.</p>","PeriodicalId":60,"journal":{"name":"The Journal of Physical Chemistry B","volume":"129 15","pages":"3928–3937 3928–3937"},"PeriodicalIF":2.8000,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photophysical and Photochemical Features of Lysine Derivatives Bearing Two Triphenylaminocinnamic-Based Fluorophores\",\"authors\":\"Mario Saletti,&nbsp;Marco Paolino,&nbsp;Jacopo Venditti,&nbsp;Gianluca Giorgi,&nbsp;Claudia Bonechi,&nbsp;Alessandro Donati,&nbsp;Claudio Rossi,&nbsp;Germano Giuliani,&nbsp;Antonella Caterina Boccia,&nbsp;Chiara Botta,&nbsp;Lluís Blancafort and Andrea Cappelli*,&nbsp;\",\"doi\":\"10.1021/acs.jpcb.5c0103210.1021/acs.jpcb.5c01032\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >A Morita–Baylis–Hillman adduct (MBHA) derivative bearing a triphenylamine (TPA) moiety was previously found to react with Nα-acetyl-<span>l</span><i>-</i>lysine methyl ester with the formation of the corresponding diadduct derivative as the major reaction product and a monoadduct as the minor one. The characterization of photochemical features of the diadduct bearing two triphenylaminocinnamic (TPAC) fluorophores suggested that this compound shows the tendency to undergo the [2 + 2] photocycloaddition reaction. This hypothesis was evaluated in the present study in both the diadduct derivatives obtained with Nα-acetyl-<span>l</span>-lysine methyl ester and Nα-acetyl-<span>l</span>-lysine. The hypothesis was confirmed in the case of the diadduct derivative obtained from Nα-acetyl-<span>l</span>-lysine methyl ester, whereas the UV-A irradiation of the diadduct derivative obtained from Nα-acetyl-<span>l</span>-lysine led to the formation of a strongly emissive (QY = 69%, λ<sub>em</sub> = 460 nm) symmetric dimer.</p>\",\"PeriodicalId\":60,\"journal\":{\"name\":\"The Journal of Physical Chemistry B\",\"volume\":\"129 15\",\"pages\":\"3928–3937 3928–3937\"},\"PeriodicalIF\":2.8000,\"publicationDate\":\"2025-04-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The Journal of Physical Chemistry B\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.jpcb.5c01032\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Physical Chemistry B","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.jpcb.5c01032","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0

摘要

先前发现含有三苯胺(TPA)片段的Morita-Baylis-Hillman加合物(MBHA)衍生物与n - α-乙酰赖氨酸甲酯反应,生成相应的二加合物衍生物为主要反应产物,次要反应产物为单加合物。对含两个三苯基氨基(TPAC)荧光团的二加合物的光化学特征表征表明,该化合物具有发生[2 + 2]光环加成反应的倾向。本研究对n - α-乙酰赖氨酸甲酯和n - α-乙酰赖氨酸得到的二加二衍生物进行了验证。以n - α-乙酰赖氨酸甲酯合成的二加二衍生物为例证实了这一假设,而n - α-乙酰赖氨酸甲酯合成的二加二衍生物经UV-A照射后形成了强发射(QY = 69%, λem = 460 nm)对称二聚体。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Photophysical and Photochemical Features of Lysine Derivatives Bearing Two Triphenylaminocinnamic-Based Fluorophores

Photophysical and Photochemical Features of Lysine Derivatives Bearing Two Triphenylaminocinnamic-Based Fluorophores

A Morita–Baylis–Hillman adduct (MBHA) derivative bearing a triphenylamine (TPA) moiety was previously found to react with Nα-acetyl-l-lysine methyl ester with the formation of the corresponding diadduct derivative as the major reaction product and a monoadduct as the minor one. The characterization of photochemical features of the diadduct bearing two triphenylaminocinnamic (TPAC) fluorophores suggested that this compound shows the tendency to undergo the [2 + 2] photocycloaddition reaction. This hypothesis was evaluated in the present study in both the diadduct derivatives obtained with Nα-acetyl-l-lysine methyl ester and Nα-acetyl-l-lysine. The hypothesis was confirmed in the case of the diadduct derivative obtained from Nα-acetyl-l-lysine methyl ester, whereas the UV-A irradiation of the diadduct derivative obtained from Nα-acetyl-l-lysine led to the formation of a strongly emissive (QY = 69%, λem = 460 nm) symmetric dimer.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
CiteScore
5.80
自引率
9.10%
发文量
965
审稿时长
1.6 months
期刊介绍: An essential criterion for acceptance of research articles in the journal is that they provide new physical insight. Please refer to the New Physical Insights virtual issue on what constitutes new physical insight. Manuscripts that are essentially reporting data or applications of data are, in general, not suitable for publication in JPC B.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信