四硫富瓦烯类衍生物的合成及表征
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摘要
以金属钠和二硫化碳为起始原料,合成四硫富瓦烯(TTF)锌的配合物(TTF)Zn(NBu_4)_2。其与卤代烷烃或取代类酰氯反应得到16个对称的四硫富瓦烯硫酮类衍生物,再经醋酸汞氧化分别得到16个四硫富瓦烯氧酮类衍生物,其中13个未见文献报道。操作简单且收率达80%以上,其结构经~1H NMR、~(13)C NMR表征确证。
(TTF)Zn(NBu_4)_2 was prepared using sodium and carbon disulfide as starting materials. 16 symmetrical TTF(thione) derivatives were synthesized from the reaction of this intermediate with brominated alkanes or substituted acyl chlorides followed by the oxidation by mercuric acetate. Thirteen compounds were firstly reported. The structures of products were confirmed by ~1H NMR and ~(13)C NMR.
(TTF)Zn(NBu_4)_2 was prepared using sodium and carbon disulfide as starting materials. 16 symmetrical TTF(thione) derivatives were synthesized from the reaction of this intermediate with brominated alkanes or substituted acyl chlorides followed by the oxidation by mercuric acetate. Thirteen compounds were firstly reported. The structures of products were confirmed by ~1H NMR and ~(13)C NMR.
引文
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[3]Bergkamp J J,Decurtins S,Liu S X.Current advances in fused tetrathiafulvalene donor-acceptor systems[J].Chem Soc Rev,201544(4):863-874.
[4]Zhao B T,Chen X H,Ma S X,et al.Synthesis of(thia)Calixarenebased ex TTF Derivatives and Their Electron Transfers Towards pChloranil and C-60[J].Chem Res Chinese U,2015,31(6):930-935
[5]李倩,耿允,段雨爱,等.卤素、氰基及N原子修饰对四硫富瓦烯衍生物载流子传输性质影响的理论研究[J].高等学校化学学报,2014,35(7):1 471-1 479.
[6]马学健,郑远志,章风清,等.含Schiff base结构新型噻吩基偶极功能分子的制备[J].精细化工中间体,2013,43(5):51-53.
[7]Nielsen M B,Nielsen S B,Becher J.'Self-complexing'tetrathiafulvalene macrocycles;a tetrathiafulvalene switch[J].Chem Commun,1998,4:475-476.
[8]Nielsen M B,Hansen J G,Becher J.Self-complexing tetrathiafulvalene-based donor-acceptor macrocycles[J].Eur JOrg Chem,1999,11:2807-2815.
[9]汪营磊,张志忠,王伯周,等.3,5-二氨基-4-苯偶氮基吡唑合成与表征[J].精细化工中间体,2007,37(4):39-40.
[10]杨超,姜文凤,王慧龙.N,N-二甲基乙酰胺缩二甲醇的合成[J].精细化工中间体,2010,40(5):55-57.
[11]Balzani V,Credi A,Mattersteig G,et al.Switching of pseudorotaxanes and catenanes incorporating a tetrathiafulvalene unit by redox and chemical inputs[J].J Org Chem,2000,65(7):1 924-1 936.
[12]尹炳柱,温全武,陈铁,等.具有纳米尺寸的四聚四硫富瓦烯大环冠醚的合成[J].有机化学,2005,25(2):188-192.
[13]Nygaard S,Leung K C-F,Aprahamian I,et al.Functionally rigid bistable[2]rotaxanes[J].J Am Chem Soc,2007,129(4):960-970.
[14]Zhang H,Duan H B,Liu Sh X,et al.A novel magnetic informational storage material[3,4-Cl2-Bz-1-APy][Ni(dmit)2]and synthetic method thereof:中国,104530137[P].2015-04-22.
[15]Terauchi T,Sumi S,Kobayashi,Y,et al.Two-dimensional brickblock arrangement in bis-fused tetrathiafulvalene semiconductors[J].Cryst Growth Des,2014,14(3):1 412-1 418.
[16]Rivadehi S,Reid E F,Hogan C F,et al.Fluoride-selective optical sensor based on the dipyrrolyl-tetrathiafulvalene chromophore[J].Org Biomol Chem,2010,10(4):705-709.
[17]Shao M,Dongare P,Dawe L N,et al.Biscrown-annulated TTFAQ-Dianthracene hybrid:synthesis,structure,and metal ion sensing[J].Org Lett,2010,12(13):3 050-3 053.
[18]Butler I R,Gerner P.The synthesis of anthracene,and dipyridine salts as cations for DMIT complexes[J].Inorg Chim Acta,2013,396:1-5.
[19]Christiansen K,Becher J,Hansen T K.Synthesis of annulated biscrown ethers[J].Tetrahedron Lett,1992,33(21):3 035-3 038.