Fluorescence behaviour of 2-, 3- and 4-amino-1,8-naphthalimides: effects of the substitution positions of the amino functionality on the photophysical properties†,Photochemical & Photobiological Sciences

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Fluorescence behaviour of 2-, 3- and 4-amino-1,8-naphthalimides: effects of the substitution positions of the amino functionality on the photophysical properties†
Photochemical & Photobiological Sciences ( IF 2.7 ) Pub Date : 2018-08-15 00:00:00 , DOI: 10.1039/c8pp00302e
Lei Wang _{1,

2,

3,

4,

5} , Mayu Fujii _{1,

2,

3,

4,

5} , Minoru Yamaji _{6,

7,

8,

9,

10} , Hideki Okamoto _{1,

2,

3,

4,

5}

Affiliation

The absorption and fluorescence spectra of a series of 1,8-naphthalimide derivatives incorporating the amino functionality at the 2-, 3- and 4-positions of the naphthalene ring (2APNI, 3APNI and 4APNI, respectively) were systematically investigated in various solvents and in the solid state. The fluorescence spectra of 2APNI were insensitive to solvent polarity and intermolecular hydrogen-bonding even in a protic medium such as methanol. Thus, 2APNI displayed blue fluorescence with a moderate fluorescence quantum yield (λ^F_max = 420–445 nm, Φ_F 0.2–0.3) in the solvents investigated. In contrast, the fluorescence spectra of 3APNI and 4APNI were strongly solvent dependent showing positive solvatofluorochromism with large Stokes shifts. Upon increasing the solvent polarity, the fluorescence colours changed from blue in hexane (λ^F_max = 429 nm) to orange-yellow in methanol (λ^F_max = 564 nm) for 3APNI, and from blue in hexane (λ^F_max = 460 nm) to yellow in methanol (λ^F_max = 538 nm) for 4APNI. The fluorescence quantum yields of 3APNI and 4APNI decreased with increasing solvent polarity. In the solid state, APNIs displayed red-shifted fluorescence emission compared to that in solution (λ^F_max = 541 nm for 2APNI, 575 nm for 3APNI, and 561 nm for 4APNI) and the fluorescence quantum yields in the solid state were lower than those in solution.

中文翻译：

2-，3-和4-氨基-1,8-萘二甲酰亚胺的荧光行为：氨基官能团的取代位置对光物理性质的影响†

在各种溶剂和溶剂中，系统地研究了一系列在萘环的2位，3位和4位（分别为2APNI，3APNI和4APNI）结合了氨基官能团的1,8-萘二甲酰亚胺衍生物的吸收光谱和荧光光谱。在固态。2APNI的荧光光谱即使在质子传递介质如甲醇中也对溶剂极性和分子间氢键不敏感。因此，2APNI显示蓝色荧光以适度的荧光量子产率（λ ^˚F_最大= 420-445纳米，Φ _˚F0.2–0.3）在所研究的溶剂中。相反，3APNI和4APNI的荧光光谱强烈依赖溶剂，显示出正的溶剂化荧光色，斯托克斯位移较大。当增加溶剂极性，荧光颜色从蓝色的己烷改变（λ ^˚F_最大= 429纳米）至橙黄色的甲醇（λ ^˚F_最大= 564纳米）为3APNI，和从蓝色在己烷（λ ^˚F_最大= 460 nm）至在甲醇黄色（λ ^˚F_最大= 538纳米）为4APNI。3APNI和3APNI的荧光量子产率4APNI随着溶剂极性的增加而降低。在固态下，APNI标准相比较，以在溶液中（显示红移荧光发射λ ^˚F_最大=为541纳米2APNI，对于575nm的3APNI，以及用于561纳米4APNI在固体状态）和荧光量子产率分别为低比解决方案中的解决方案好。

更新日期：2018-08-15

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