Synthesis of Naphthalimide Derivatives and Its Recognition for Picric Acid

YU Ying-hao; DU Bin; DING Zhi-jun; WANG Pu-hong; GUO Lei; YU Jian-hua; HU Yu-lai

doi:10.3788/fgxb20153601.0039

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Synthesis of Naphthalimide Derivatives and Its Recognition for Picric Acid

更新时间：2020-08-12

- Synthesis of Naphthalimide Derivatives and Its Recognition for Picric Acid
- Chinese Journal of Luminescence Vol. 36, Issue 1, Pages: 39-44(2015)
- 作者机构：
  
  1. 西北师范大学化学化工学院,甘肃兰州,730070
  2. 防化研究院北京,102205
- 作者简介：
- 基金信息：
- DOI：10.3788/fgxb20153601.0039
  CLC： O644
- Received：11 October 2014，
  
  Revised：05 November 2014，
  
  Published：03 January 2015
- 稿件说明：
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余颖昊, 杜斌, 丁志军等. 萘酰亚胺衍生物的合成及对苦味酸的检测[J]. 发光学报, 2015,36(1): 39-44

YU Ying-hao, DU Bin, DING Zhi-jun etc. Synthesis of Naphthalimide Derivatives and Its Recognition for Picric Acid[J]. Chinese Journal of Luminescence, 2015,36(1): 39-44
余颖昊, 杜斌, 丁志军等. 萘酰亚胺衍生物的合成及对苦味酸的检测[J]. 发光学报, 2015,36(1): 39-44 DOI： 10.3788/fgxb20153601.0039.

YU Ying-hao, DU Bin, DING Zhi-jun etc. Synthesis of Naphthalimide Derivatives and Its Recognition for Picric Acid[J]. Chinese Journal of Luminescence, 2015,36(1): 39-44 DOI： 10.3788/fgxb20153601.0039.

摘要

设计并合成了萘酰亚胺衍生物

-正己基-4-[2-(3-苯基硫脲)-乙氨基]-1

8-萘酰亚胺(HTN)

通过NMR和MS表征了其结构。利用荧光光谱法研究了HTN对苦味酸(PA)的识别作用。研究发现

在C

OH/H

O (2:1)体系中

HTN荧光强度随PA浓度的增加而大幅度下降。PA浓度在110

-6

~510

-4

molL

-1

范围内时

猝灭率(I

-I)/I

与[PA]

0.5

呈线性关系

=0.995 5。常见苯系物

如苯胺、苯甲醛、三硝基甲苯、苯酚、苯乙烯、吡啶、对甲苯磺酸、甲苯、硝基苯及氯苯等均不干扰HTN对PA的识别。结果表明

HTN对PA具有较好的选择性和灵敏度。

Abstract

-hexyl-4-[2-(3-phenyl-thiourea)-ethylamino]-naphthalimide (HTN)

a naphthalimide derivative

was synthesized and its structure was determined by NMR and MS. The recognition of HTN for picric acid (PA) was investigated by fluorescence spectrum. The results show that the fluorescence intensity of HTN significantly reduces with the increasing of PA concentration in C

OH/H

O (2:1). For PA concentration from 110

-6

molL

-1

to 510

-4

molL

-1

the quenching rate

-I)/I

correlates linearly with [PA]

0.5

and

=0.995 5. Meanwhile

no obvious interference is observed in the presence of the benzene series such as aniline

benzaldehyd

trinitrotoluene

phenol

styrene

pyridine

p-toluenesulfonic acid

toluene

nitrobenzene and chlorobenzene

indicating HTN's excellent selectivity and high sensitivity for the detection of PA.

关键词

Keywords

references

Shi Y J, Ma Y X, Chui M, et al. Determination of picric acid by gas phase chromatography [J]. Inner Mongolia Petrochem. Industry (内蒙古石油化工), 2014(7):9-10 (in Chinese).

Zhao H S, Chang M, Liu B X, et al. Quickly determination of picric acid in water by high performance liquid chromatography [J]. Environmental Monitoring in China (中国环境监测), 2013, 29(4):135-137 (in Chinese).

Cui F Y, Zhou P, Wang W M, et al. Progress of method for determination of picric acid in water [J]. Norhern Environmental (北方环境), 2013, 25(7):155-158 (in Chinese).

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Singh K, Chaudhary G R, Mehta S K, et al. Synthesis of highly luminescent water stable ZnO quantum dots as photoluminescent sensor for picric acid [J]. J. Lumin., 2014, 154:148-154.

Huang J R, Wang L Y, Gu C P, et al. Selective detection of picric acid using functionalized reduced graphene oxide sensor device [J]. Sens. Actuat., B: Chem., 2014, 196:567-573.

Yun S W, Kang N Y, Park S J, et al. Diversity oriented fluorescence library approach (DOFLA) for live cell imaging probe development [J]. Acc. Chem. Res., 2014, 47(4):1277-1286.

Sorokin A V, Zabolotskii A A, Pereverzev N V, et al. Plasmon controlled exction fluorescence of molecular aggregates [J]. J. Phys. Chem. C, 2014, 118(14):7599-7605.

Tanaka H, Shizu K, Nakanotani H, et al. Dual intramolecular charge-transfer fluorescence derived from a phenothiazine-triphenyltriazine derivative [J]. J. Phys. Chem. C, 2014, 118(29):15985-15994.

Chen J, He Y, Wang J A, et al. Synthesis and optoelectronic properties of aromatic polyethers with a 1,8-naphthalimide unit main chain [J]. Chin. J. Lumin.(发光学报), 2012, 33(3):243-246 (in Chinese).

Zhang Y H, Zhang Q P, Shi W Y, et al. Synthesis and quantum chemistry study on fluorescence spectra of three 1,8-naphthalimide monomers [J]. Chin. J. Lumin.(发光学报), 2011, 32(5):505-513 (in Chinese).

Tian J, Chen B, Lv H, et al. Progress in fluorescence resonance energy transfer probes for detection of cation ions based on 1,8-naphthalimide [J]. Appl. Chem. Ind.(应用化工), 2014, 43(2):346-352 (in Chinese).

Langdon-Jones E E, Symonds N O, Yates S E, et al. Fluorescent rhenium-naphthalimide conjugates as cellular imaging agents [J]. Inorg. Chem., 2014, 53:3788-3797.

Mahato P, Saha S, Suresh E, et al. Ratiometric detection of Cr3+ and Hg2+ by a naphthalimide-rhodamine based fluorescent probe [J]. Inorg. Chem., 2012, 51:1769-1777.

Panchenko P A, Fedorov Y V, Perevalov V P, et al. Cation-dependent fluorescent properties of naphthalimide derivatives with N-benzocrown ether fragment [J]. J. Phys. Chem. A, 2010, 114:4118-4122.

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