62135-59-5Relevant academic research and scientific papers
Molecular Engineering of Mechanochromic Materials by Programmed C-H Arylation: Making a Counterpoint in the Chromism Trend
Wu, Jie,Cheng, Yangyang,Lan, Jingbo,Wu, Di,Qian, Shengyou,Yan, Lipeng,He, Zhen,Li, Xiaoyu,Wang, Kai,Zou, Bo,You, Jingsong
supporting information, p. 12803 - 12812 (2016/10/13)
The development of facile methods for screening organic functional molecules through C-H bond activation is a revolutionary trend in materials research. The prediction of mechanochromism as well as mechanochromic trends of luminogens is an appealing yet challenging puzzle. Here, we present a strategy for the design of mechanochromic luminogens based on the dipole moment of donor-acceptor molecules. For this purpose, a highly efficient route to 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines (2,7-diaryl-TAPs) has been established through programmed C-H arylation, which unlocks a great opportunity to rapidly assemble a library of fluorophores for the discovery of mechanochromic regularity. Molecular dipole moment can be employed to explain and further predict the mechanochromic trends. The 2,7-diaryl-TAPs with electron-donating groups on the 2-aryl and electron-withdrawing groups on the 7-aryl possess a relatively small dipole moment and exhibit a red-shifted mechanochromism. When the two aryls are interchanged, the resulting luminogens have a relatively large dipole moment and display a blue-shifted mechanochromism. Seven pairs of isomers with opposite mechanochromic trends are presented as illustrative examples. The aryl-interchanged congeners with a bidirectional emission shift are structurally similar, which provides an avenue for understanding in-depth the mechanochromic mechanism.
Synthesis of 2-Aryl-1,2,4-triazolopyrimidines
Prasad, V.S.R.,Reddy, K.Kondal
, p. 2617 - 2622 (2007/10/02)
N-2-Pyrimidylarylamidines (2) obtained by the reaction of 2-aminopyrimidines (1) with aryl cyanides in the presence of anhydrous aluminium chloride have been converted into 2-aryl-1,2,4-triazolopyrimidines (4) by oxidative cyclisation in the presence of lead tetraacetate.
Synthesis of 2-Aryltriazolopyrimidines
Kamala, K.,Rao, P. Jayaprasad,Reddy, K. Kondal
, p. 3791 - 3793 (2007/10/02)
2-Aroylamino)pyrimidines (4) have been converted into 1-(2-pyrimidyl)-5-aryl-1H-tetrazoles (6) by treatment with PCl5 followed by azidolysis in aqueous acetone solution.Pyrolysis of 6 in decalin gave 2-aryltriazolopyrimidines (8).A reasonable pathway for the formation of 8 from 6 is suggested.Structures of all the compounds have been established by elemental analysis and spectral data.
