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N-苄叉萘-1-胺呈现的依赖表面活性剂的pH控制的“开-关”、“开-关-关”和“关-开”荧光开关

Surfactant Dependent pH Controlled "off-on", "off-on-off" and "on-off" Fluorescent Switches Exhibited by N-Benzylidenenaphthalen-1-Amine.

作者信息

Kumar Jutika, Sarma Manas Jyoti, Phukan Prodeep, Das Diganta Kumar

机构信息

Department of Chemistry, Gauhati University, Guwahati, Assam, India, 781 014.

出版信息

J Fluoresc. 2015 Sep;25(5):1431-5. doi: 10.1007/s10895-015-1633-y. Epub 2015 Aug 19.

DOI:10.1007/s10895-015-1633-y
PMID:26282918
Abstract

N-benzylidenenaphthalen-1-amine (L) acts as pH dependent "off-on", "off-on-off" and "on-off" fluorescent switch in 1:1 (v/v) CH3CN:H2O depending on the presence of anionic sodiumdocdecyl sulphate (SDS), neutral triton X-100 (TX-100) and cationic cetyltrimethylammonium bromide (CTAB) surfactants respectively. DFT calculation shows the possibility of formation of L.H(+) due to protonation at immine N and L.OH(-) due to introduction of OH(-) group at immine C. The relative stability of these two cationic and anionic species depends on the charge environment provided by surfactants. This influences the photoinduced electron transfer (PET) processes involved and results in different switch behaviour.

摘要

N-亚苄基萘-1-胺(L)在1:1(v/v)的乙腈:水体系中,根据阴离子十二烷基硫酸钠(SDS)、中性曲拉通X-100(TX-100)和阳离子十六烷基三甲基溴化铵(CTAB)表面活性剂的存在情况,分别充当pH依赖型“关-开”、“关-开-关”和“开-关”荧光开关。密度泛函理论计算表明,由于亚胺N处的质子化,可能形成L.H(+),以及由于亚胺C处引入OH(-)基团,可能形成L.OH(-)。这两种阳离子和阴离子物种的相对稳定性取决于表面活性剂提供的电荷环境。这会影响所涉及的光致电子转移(PET)过程,并导致不同的开关行为。

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