Systematic synthesis, comparative studies of the optical properties, and the ICT-based sensor properties of a series of 2,4,6-tri(5-aryl-2-thienyl)pyrimidines with the D-pi-A system

作者：Muraoka Hiroki^*; Obara Takumi; Ogawa Satoshi^*

来源：Tetrahedron Letters, 2016, 57(27-28): 3011-3015.

DOI：10.1016/j.tetlet.2016.05.099

• Thiophene
• Pyrimidine
• Intramolecular charge transfer
• Solvatochromism
• Proton-sensing

A series of 2,4,6-tri(5-aryl-2-thienyl)pyrimidines with a star-shaped D-pi-A system, which have an electron deficient pyrimidine core (A) and three donor type aryl groups (D) linked by a thiophene spacer (pi-spacer), were designed and systematically synthesized. Through the characterization of the molecules by UV-vis absorption and fluorescence spectroscopies, we revealed that the molecules possess distinct absorption and emission wavelengths controlled by the donor effect of the terminal aryl groups. Interestingly, 2,4,6-tris(5-p-N,N-dibutylaminophenyl-2-thienyl)pyrimidine was found to exhibit strong fluorosolvatochromic properties and a proton-sensibility based on its intramolecular charge transfer (ICT) and basic characteristics, which could allow its use as a polarity or proton sensor.

• 出版日期2016-7-6