Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing

被引：15

作者：

Tigoianu, Radu ^{[1
]}

Airinei, Anton ^{[1
]}

Georgescu, Emilian ^{[2
,3
]}

Nicolescu, Alina ^{[1
]}

Georgescu, Florentina ^{[4
]}

Isac, Dragos Lucian ^{[1
]}

Deleanu, Calin ^{[1
,2
]}

Oancea, Florin ^{[5
]}

机构：

[1] Romanian Acadx, Petru Poni Inst Macromol Chem, Aleea Grigore Ghica Voda 41A, Iasi, Romania

[2] Romanian Acad, CD Nenitescu Ctr Organ Chem, Splaiul Independentei 202B, Bucharest, Romania

[3] Chimcomplex SA, Res Ctr, St Uzinei 1, Bucharest, Romania

[4] Enpro Soctech Com Srl, Str Elefterie 51, Bucharest, Romania

[5] Natl Res & Dev Inst Chem & Petrochem ICECHIM, Splaiul Independentei 202B, Bucharest, Romania

来源：

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES | 2022年 / 23卷 / 05期

关键词：

piperidine-1; 8-naphthalimide; solvatochromism; solvent dependent emission; water sensor; fluorescence lifetime; PHOTOPHYSICAL PROPERTIES; ABSORPTION-SPECTRA; SPECTROSCOPIC PROPERTIES; HYPOCHLOROUS ACID; ORGANIC-SOLVENTS; PI-STAR; 1,8-NAPHTHALIMIDE; SENSOR; GERMINATION; IMMOBILIZATION;

D O I：

10.3390/ijms23052760

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Novel fluorescent strigolactone derivatives that contain the piperidine-substituted 1,8-naphthalimide ring system connected through an ether link to a bioactive 3-methyl-furan-2-one unit were synthesized and their spectroscopic properties investigated. The solvatochromic behavior of these piperidine-naphthalimides was monitored in solvents of different polarity using the electronic absorption and fluorescence spectra. These compounds exhibited a strong positive solvatochromism taking into account the change of solvent polarity, and the response mechanism was analyzed by fluorescence lifetime measurements. According to Catalan and [f(n), f(epsilon), beta, alpha] solvent scales, the dipolarity and polarizability are relevant to describe the solute-solvent interactions. The emission chemosensing activity was discussed in order to determine the water content in organic environments. The emission intensity of these compounds decreased rapidly in dioxane, increasing water level up to 10%. Measuring of quantum yield indicated that the highest values of quantum efficiency were obtained in nonpolar solvents, while in polar solvents these derivatives revealed the lowest quantum yield. The fluorescence decay can be described by a monoexponential model for low water levels, and for higher water contents a biexponential model was valid.

引用

页数：21

共 22 条

[21] Expedient multicomponent synthesis of a small library of some novel highly substituted pyrido[2,3-d]pyrimidine derivatives mediated and promoted by deep eutectic solvent and in vitro and quantum mechanical study of their antibacterial and antifungal activities
Reza Aryan
Hamid Beyzaei
Masoomeh Nojavan
Fatemeh Pirani
Hojat Samareh Delarami
Mahmood Sanchooli
Molecular Diversity, 2019, 23 : 93 - 105
[22] Expedient multicomponent synthesis of a small library of some novel highly substituted pyrido[2,3-d]pyrimidine derivatives mediated and promoted by deep eutectic solvent and in vitro and quantum mechanical study of their antibacterial and antifungal activities
Aryan, Reza
Beyzaei, Hamid
Nojavan, Masoomeh
Pirani, Fatemeh
Delarami, Hojat Samareh
Sanchooli, Mahmood
MOLECULAR DIVERSITY, 2019, 23 (01) : 93 - 105

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