合成了2个新型氨基硫脲分子钳主体3a(1,3-二(ο-甲苯氧乙酰氨基硫脲甲酰基)苯)和3b(1,3-二(p-甲苯氧乙酰氨基硫脲甲酰基)苯),利用UV-Vis和1H NMR测试其对F-、AcO -、Cl-、Br-和I-的阴离子识别性质.结果表明,主体分子在DMSO溶液中对F-和AcO -表现出明显的选择性识别.1H NMR光谱证明,主体分子与阴离子之间以氢键相结合,结合Job曲线得出主体分子与阴离子之间形成1∶1型氢键缔合物.讨论了NH识别位点数及空间结构对识别性质的影响.与硫脲对比,主体3a具有多个NH结合位点,可形成多个氢键,结合常数(Ks)更大.与化合物3b相比,主体3a较大的空间位阻阻碍了其与阴离子的结合,因此两种主体分子与F-和AcO -结合常数均体现为Ks(F-)>Ks(AcO-).
参考文献
[1] | He J J,Quiocho F A.A Nonconservative Serine to Cysteine Mutation in the Sulfate-binding Protein,A Transport Receptor[J].Science,1991,251(5000):1479-1481. |
[2] | Berryman O B,Bryantsev V S,Stay D P,et al.The Interaction of Halides with Electron-deficient Arenes[J].Am Chem Soc,2007,129(1):48-58. |
[3] | Amendola V,Esteban-Gomez D,Fabbrizzi L,et al.What Anions Do to N-H-containing Receptors[J].Acc Chem Res,2006,39(5):343-353. |
[4] | Kondo S I,Harada T,Tanaka R,et al.Anion Recognition by a Silanediol-based Receptor[J].Org Lett,2006,8 (20):4621-4624. |
[5] | XU Sheng,LIU Bin,TIAN He.Progress on Fluorescent Chemosensors for Anions[J].Prog Chem,2006,18(6):687-697(in Chinese).许胜,刘斌,田禾.阴离子荧光化学传感器新进展[J].化学进展,2006,18(6):687-697. |
[6] | Suksai C,Tbntulani T.Chromogenic Anion Sensors[J].Chem Soc Rev,2003,32(4):192-202. |
[7] | Beer P D,Gale P A.Anion Recognition and Sensing:the State of the Art and Future Perspectives[J].Angew Chem Int Ed,2001,40(3),486-516. |
[8] | Yen Y P,Ho K W.Development of Colorimetric Receptors for Selective Discrimination Between Isomeric Dicarboxylate Anions[J].Tetrahedron Lett,2006,47(41):7357-7360. |
[9] | Pfeffer F M,Gunnlaugsson T,Jensen P,et al.Anion Recognition Using Preorganized Thiourea Functionalized[3]Polynorbornane Receptors[J].Org Lett,2005,7 (24):5357-5360. |
[10] | Gale P A.Structural and Molecular Recognition Studies with Acyclic Anion Receptors[J].Acc Chem Res,2006,39 (7):465-475. |
[11] | ZHAO Zhigang,LIU Xingli,LI Qinghan,et al.Progress in Research on Molecular Tweezer Artificial Receptors[J].Chinese J Org Chem,2009,29(9):1336-1353(in Chinese).赵志刚,刘兴利,李清寒,等.分子钳人工主体研究进展[J].有机化学,2009,29(9):1336-1353. |
[12] | Wei Taibao,Wei Wei,Cao Cheng,et al.Synthesis and Anion Recognition of Molecular Tweezers Receptors Based on Acylthiourea[J].Phosphorus Sulfur Silicon Relat Elem,2008,183 (5):1218-1228. |
[13] | ZHANG Youming,CAO Cheng,WEI Wei,et al.Crystal Structure of Thiourea Derivatives Based Tweezer Receptors and Its Selective Recognition of Fluoride Ion by Hydrogen Bonding[J].Acta Chim Sin,2007,65(24):2947-2951 (in Chinese).张有明,曹成,魏薇,等.基于硫脲衍生物的钳形分子主体的晶体结构及其对F-离子的选择性识别[J].化学学报,2007,65(24):2947-2951. |
[14] | Wei Wei,Wei Taibao.Synthesis and Anion Recognition of Novel Molecular Tweezer Receptor Based on Carbonyl Thiosemicarbazide for Fluoride Ions[J].Chinese J Chem,2008,26(10):1935-1938. |
[15] | Zhang Youming,Wang Dandan,Lin Qi,et al.Synthesis and Anion Recognition Properties of Thiosemicarbazone Based on Molecular Tweezers[J].Phosphorus Sulfur Silicon Relat Elem,2008,183(1):44-55. |
[16] | ZHANG Youming,REN Haixian,WEI Taibao.Synthesis of Isophthalic Aldehyde Bis-arylthiosemicarbazone and Their Anion Recognition Properties[J].Chem J Chinese Univ,2006,27 (11):2079-2083 (in Chinese).张有明,任海鲜,魏太保.间苯二甲醛缩双芳氨基硫脲的合成及阴离子识别研究[J].高等学校化学学报,2006,27(11):2079-2083. |
[17] | Wei Taibao,Wei Wei,Cao Cheng,et al.The Anion Recognition of Simple-structure Molecular Tweezers Receptors Based on Acyl-thiourea[J].Indian J Chem,2007,46B (7):1028-1032. |
[18] | Liu Yu,Kang Shizhao,Li Li.Synthesis of Novel b-Cyclodextrin Derivatives Bearing a 1-Naphthyloxamino-oligo (ethyleneamino) Moiety and Their Inclusion Complexation with Some Fluorescent Dyes[J].Supramol Chem,2002,14(4):329-337. |
[19] | WU Fangying,WEN Zhenchang,JIANG Yunbao.Thiourea-based Receptors for Anion Recognition and Sensing[J].Prog Chem,2004,16 (5):776-784 (in Chinese).吴芳英,温珍昌,江云宝.硫脲类阴离子受体的研究进展[J].化学进展,2004,16(5):776-784. |
[20] | ZHANG Youming,WANG Aixia,LENG Yanli,et al.1,3-Benzyldiacyl Hydrazone Tweezers Receptors:Synthesis and an Ions Recognition Properties[J].Chinese J Appl Chem,2009,26 (11):1253-1258 (in Chinese).张有明,王爱霞,冷艳丽,等.间苯二甲酰腙衍生物的合成及阴离子识别[J].应用化学,2009,26(11):1253-1258. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%