Synthesis ( IF 2.2 ) Pub Date : 2018-12-13 , DOI: 10.1055/s-0037-1611368 Andrea Nitti 1 , Dario Pasini 1 , Gabriele Bianchi 2 , Riccardo Po 2
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Abstract
The synthesis on a gram-scale and the full characterization of naphtho[1,2-b]thiophene and benzo[1,2-b:6,5-b']dithiophene 4-carboxylate esters bearing 2-octyldodecyl side chains, and their stannylated and brominated derivatives, suitable for their insertion into π-conjugated polymers is described. The fully soluble and processable synthons are obtained through a cascade sequence of reactions, namely direct arylation and cross aldol condensation, which create an effective pathway for the annulation and π-extension of suitable, commercially available reagents. The newly reported synthesis are compared, whenever possible, using ‘green chemistry metrics’ with literature synthesis, showing dramatic improvements.
The synthesis on a gram-scale and the full characterization of naphtho[1,2-b]thiophene and benzo[1,2-b:6,5-b']dithiophene 4-carboxylate esters bearing 2-octyldodecyl side chains, and their stannylated and brominated derivatives, suitable for their insertion into π-conjugated polymers is described. The fully soluble and processable synthons are obtained through a cascade sequence of reactions, namely direct arylation and cross aldol condensation, which create an effective pathway for the annulation and π-extension of suitable, commercially available reagents. The newly reported synthesis are compared, whenever possible, using ‘green chemistry metrics’ with literature synthesis, showing dramatic improvements.
中文翻译：
萘噻吩和苯并二噻吩支架的可扩展合成作为π共轭合成子的有机材料
摘要
克级合成并带有2-辛基十二烷基侧链的萘并[1,2- b ]噻吩和苯并[1,2- b：6,5- b' ]二噻吩4-羧酸酯的完整表征，以及描述了适合于它们插入π-共轭聚合物中的它们的甲氧基化和溴化衍生物。完全可溶且可加工的合成子是通过级联反应序列获得的，即直接芳基化和交叉羟醛缩合，这为适当的可商购试剂的环化和π延伸创造了一条有效途径。只要有可能，就将新报告的合成与文献合成相比较，使用“绿色化学指标”进行比较，从而显示出巨大的进步。
克级合成并带有2-辛基十二烷基侧链的萘并[1,2- b ]噻吩和苯并[1,2- b：6,5- b' ]二噻吩4-羧酸酯的完整表征，以及描述了适合于它们插入π-共轭聚合物中的它们的甲氧基化和溴化衍生物。完全可溶且可加工的合成子是通过级联反应序列获得的，即直接芳基化和交叉羟醛缩合，这为适当的可商购试剂的环化和π延伸创造了一条有效途径。只要有可能，就将新报告的合成与文献合成相比较，使用“绿色化学指标”进行比较，从而显示出巨大的进步。
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