A convenient synthetic approach to 5-aryl-2,2′-bipyridines bearing a (poly)fluorine-containing aniline residue at position C6 based on sequential ipso-substitution of the cyano group at position C5 of 3-(2-pyridyl)-1,2,4-triazines and the aza-Diels–Alder reaction has been proposed. The influence of the number and the position of the fluorine atoms on the reactivity of fluoroanilines has been estimated by means of DFT calculations. It was shown that the reaction cannot be realized if a nitro group is present in the ortho-position or two fluorine atoms occupied the ortho-positions in aniline. Photophysical properties of prospective “push–pull” fluorophores have been studied. Incorporation of fluorine atom into position 4 of aniline fragment in 5-p-tolylbipyridines causes small bathochromic shift of emission maximum, whereas the replacement of the methoxy group at the position C4 of the aniline moiety in 5-(4-methoxyphenyl)-2,2′-bipyridine with fluorine atom leads to a significant hypsochromic shift of emission maximum and to significant increase in quantum yield; the positive solvatochromism has been observed.

基于3-（2-吡啶基）-在C5位的氰基的顺次ipso-取代，对C6位带有（多）含氟苯胺残基的5-芳基-2,2'-联吡啶的简便合成方法1,2,4-三嗪和aza-Diels-Alder反应已被提出。氟原子的数量和位置对氟苯胺反应性的影响已经通过DFT计算来估算。结果表明，如果在邻位上存在硝基或两个氟原子占据苯胺的邻位，则该反应无法实现。已经研究了预期的“推挽”荧光团的光物理性质。将氟原子结合到5- p中苯胺片段的4位-tolylbipyridines引起最大发射的小红移，而5-（4-甲氧基苯基）-2,2'-联吡啶中苯胺部分C4位置的甲氧基被氟原子取代会导致显着的Hyp变色移。发射最大值并显着增加量子产率；观察到阳性溶剂变色。