以2,4-二氯-6-辛氧基-1,3,5-三嗪为原料,经Kumada偶联及胺化两步反应合成了三嗪胺衍生物:4-(9-蒽基)-6-辛氧基-1,3,5-三嗪-2-胺(AOOTA), 总产率为 38%.通过紫外-可见吸收光谱及荧光光谱研究了氯仿溶液中AOOTA在乙酸(HOAc) 及三氟乙酸 (TFA) 作用下的光谱行为.研究发现AOOTA与HOAc在基态及激发态下均不能发生双氢键作用,而AOOTA与TFA相互作用基态下形成双氢键复合物, 激发态下由于分子中蒽基及辛氧基与三嗪环间的C-C单键以及C-O单键的自由旋转,从而使得AOOTA与TFA分子间不能形成有效的氢键相互作用.
参考文献
| [1] | Grzegorz B .Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic synthesis[J].Tetrahedron,2006,62:9507-9522. |
| [2] | Wang MX .Heterocalixaromatics, new generation macrocyclic host molecules in supramolecular chemistry[J].Chemical communications,2008(38):4541-4551. |
| [3] | Bao-Yong Hou;De-Xian Wang;Hai-Bo Yang .Synthesis and Structure of Upper-Rim 1,3-Alternate Tetraoxacalix[2]arene[2]triazine Azacrowns and Change of Cavity in Response to Fluoride Anion[J].The Journal of Organic Chemistry,2007(14):5218-5226. |
| [4] | Hai-Bo Yang;De-Xian Wang;Qi-Qiang Wang;Mei-Xiang Wang .Efficient Functionalizations of Heteroatom-Bridged Calix[2]arene[2]triazines on the Larger Rim[J].The Journal of Organic Chemistry,2007(10):3757-3763. |
| [5] | Takashi Murase;Makoto Fujita .Highly Blue Luminescent Triazine-Amine Conjugated Oligomers[J].The Journal of Organic Chemistry,2005(23):9269-9278. |
| [6] | Ishikawa H;Iwata K;Hamaguchi H .Picosecond dynamics of stepwise double proton-transfer reaction in the excited sate of the 2-aminopyridine/acetic acid system[J].Journal of Physical Chemistry A,2002,106:2305-2312. |
| [7] | Kitamura T;Hikita A;Ishikawa H;Fujimoto A .Photoinduced amino-imino tautomerization reaction in 2-aminopyrimidine and its methyl derivatives with acetic acid[J].Spectrochimica acta, Part A. Molecular and biomolecular spectroscopy,2005(4-5):1157-1164. |
| [8] | 李宗耀,李建辉,赵春梅,王华.4-（9-蒽基）-6-十六烷氧基-2-氨基-1,3,5-三嗪的合成及光谱行为的研究[J].影像科学与光化学,2009(05):325-333. |
| [9] | Benesi M L;Hildebrand J H .A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons[J].Journal of the American Chemical Society,1949,71:2703-2707. |
| [10] | M. A. El-Kemary;H. S. El-Gezawy;H. Y. El-Baradie;R. M. Issa .Excited-state double-proton transfer of pyrimidines mediated by hydrogen-bonded complexes[J].Chemical Physics: A Journal Devoted to Experimental and Theoretical Research Involving Problems of Both a Chemical and Physical Nature,2001(2):233-242. |
| [11] | Konijnenberg J;Huizer A H;Varma C A G O .A time-resolved study of the photoinduced tautomerization of 2-aminopyridine and derivatives within specific 1∶1 complexes with carboxylic acids[J].Journal of the Chemical Society,Faraday Transactions,1989,85(09):1539-1551. |
| [12] | Weisstuch A;Testa A C .A fluorescence study of aminopyridines[J].Journal of Physical Chemistry,1968,72(06):1982-1987. |
| [13] | Inuzuka K;Fujimoto A .Electronic properties and ultraviolet absorption spectra of 2-pyridinamine[J].Spectrochimica Acta Part,1986,42A(08):929-937. |
| [14] | Kitamura T;Mochida N;Okita M;Motohashi M;Ishikawa H;Fujimoto A .The hydrogen bonding and amino-imino tautornerization of the alkoxy-aminopy ridines and amino-methoxypyrimidines with acetic acid The effects of the methoxy group[J].Spectrochimica acta, Part A. Molecular and biomolecular spectroscopy,2007(3):979-991. |
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