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Synthesis and optical properties of 2-functionally substituted 4,5-dihydrothieno[3,2-c]quinolines
Dyes and Pigments ( IF 4.5 ) Pub Date : 2018-06-27 , DOI: 10.1016/j.dyepig.2018.06.031
Yulia P. Bogza , Alexey A. Rastrepin , Victoria V. Nider , Tatyana Yu Zheleznova , Anton J. Stasyuk , Aleksandra Kurowska , Katarzyna Laba , Evgeny B. Ulyankin , Wojciech Domagala , Alexander S. Fisyuk

N-Protected 4-(anilinomethyl)thiophene-2-carbaldehydes were prepared by the reaction of easily available 4-chloromethylthiophene-2-carbaldehyde with N-(2-halogenophenyl) substituted acetamides, 4-methylbenzenesulfonamides and carbamates in the presence of K2CO3 or Cs2CO3. The compounds obtained were converted to 4,5-dihydrothieno [3,2-c]quinoline-2-carbaldehydes by palladium catalyzed intramolecular cyclization in homogenous or heterogenous (Pd/C) conditions with good yields and subsequently used for preparing of 2-functionally substituted thieno [3,2-c]quinoline derivatives (nitriles, carboxamides, carboxylic acids, esters). The optical properties of 2-functionally substituted thieno[3,2-c]quinolines and 4H-thieno[3,2-c]chromenes have been studied. Moderate to high fluorescence quantum yields are observed for these compounds ranging from 0.15 to 0.87. Structure - optical properties relationships have been established for the compounds synthesized, and their prospective application as invisible ink dyes was practically demonstrated.



中文翻译:

2-官能团取代的4,5-二氢噻吩并[3,2- c ]喹啉的合成及光学性质

通过在K 2的存在下容易获得的4-氯甲基噻吩-2-甲醛与N-(2-卤代苯基)取代的乙酰胺,4-甲基苯磺酰胺和氨基甲酸酯的反应来制备N保护的4-(苯胺基甲基)噻吩-2-甲醛CO 3或Cs 2 CO 3。通过钯催化的分子内环化反应,在均相或异相(Pd / C)条件下以良好的收率将所得化合物转化为4,5-二氢噻吩并[3,2- c ]喹啉-2-甲醛。取代噻吩[3,2- c]喹啉衍生物(腈,羧酰胺,羧酸,酯)。2-功能性的光学特性被取代的噻吩并[3,2- c ^ ]喹啉和4H-噻吩并[3,2- c ^ ]色烯进行了研究。对于这些化合物,观察到中等至高的荧光量子产率,范围为0.15至0.87。已经建立了所合成化合物的结构-光学性质关系,并且已实际证明了它们作为不可见油墨染料的前瞻性应用。

更新日期:2018-06-27
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