CN114890983A - 一种羟基取代的硫杂芴的制备方法 - Google Patents
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Abstract
本发明提供了一种羟基取代的硫杂芴的制备方法，涉及有机合成领域。本发明的化合物合成路线较短，产物的分离纯化操作工艺简便、原料易得、产率较高、适宜于大量合成。本发明的产物分子中包含多个羟基，不仅可以增强给电子能力，使其具有更长波长的发射光，还可以赋予化合物更多的修饰位点，因而在有机功能材料领域具有广阔的应用前景。
Description
技术领域
本发明涉及有机合成技术领域，特别涉及一种羟基取代的硫杂芴的制备方法。
背景技术
硫杂芴衍生物是一类重要的有机合成中间体，在生物医学、有机光电和智能材料等领域有着广泛的应用。其中具有给体-受体-给体结构的硫杂芴衍生物一直是人们研究的重点。给体-受体-给体结构可以使分子形成有效的分子内电荷转移效应，实现长波长的发射。同时，硫原子可以有效增加n→π*的跃迁方式，可以增强系间窜越，有助于开发具有更深穿透深度的生物成像试剂和光动力试剂。因此，设计合成具有给体-受体-给体结构的硫杂芴衍生物具有重要意义。
三苯胺基团是目前给电子能力最强的基团之一，将三苯胺结构单元与硫杂芴结合起来是构筑具有强给体-受体-给体结构硫杂芴衍生物的一种有效方法。另外，羟基也是一种具有强给电子能力的基团，将羟基引入到三苯胺结构单元中可以获得更强的给电子能力。另一方面，羟基易于发生取代、氧化等反应，可以赋予化合物更多的修饰位点。
发明内容
本发明的目的在于提供2,8-二(4-(N,N-二(4-羟基苯基)胺基)苯基)硫杂芴的制备方法。本发明提供的目标产物合成路线短，分离纯化操作较为简便。
本发明提供了一种羟基取代的硫杂芴的制备方法，其特征在于，具有式2所示结构：
本发明提供的一种羟基取代的硫杂芴的制备方法，包括以下合成步骤：
(1)将一定量的2,8-二溴硫杂芴、4-[N,N-二(4-二甲氧基苯基)胺基]苯硼酸频哪醇酯、四(三苯基膦)钯、碳酸钠和一定量的甲苯在反应瓶中混合，加热到一定温度，在该温度下搅拌反应一定的时间，反应混合物经溶剂稀释、萃取、分离、干燥及回收溶剂等步骤得到粗产物，利用柱层析分离得到目标产物的溶液，回收溶剂后得到化合物1。
(2)将一定量的化合物1溶解在一定量的二氯甲烷中，在一定温度下加入17%的三溴化硼二氯甲烷溶液，在该温度下搅拌反应一定的时间，将温度升高到另一温度，在该温度下搅拌反应一定的时间，反应混合物经猝灭、溶剂稀释、萃取、分离、干燥及回收溶剂等步骤得到粗产物，利用柱层析分离得到目标产物的溶液，回收溶剂后得到化合物2。
本发明提供的2,8-二(4-(N,N-二(4-羟基苯基)胺基)苯基)硫杂芴具有给体-受体-给体结构，依次通过铃木偶联反应和水解反应即可合成。羟基的引入不仅可以增强给电子能力，使其具有更长波长的发射光，还可以赋予化合物更多的修饰位点。有效提高了目标产物在生物医学等领域的应用能力。
本发明提供了所述化合物的制备方法，本发明提供的制备方法步骤简便，分离及纯化过程易操作，原料易得，产率较高，适合放大量合成及今后的规模化生产。
具体实施方式
实施例
(1)将342 mg 2,8-二溴硫杂芴、905 mg 4-[N,N-二(4-二甲氧基苯基)胺基]苯硼酸频哪醇酯、208 mg四(三苯基膦)钯、318 mg碳酸钠和8 mL甲苯在反应瓶中混合，搅拌5min使原料充分溶解，在氮气的保护下，95 ℃条件下搅拌反应16 h。反应结束后降至室温，用30 mL二氯甲烷稀释反应液并转移到分液漏斗中，有机相用饱和氯化铵水溶液洗涤两次，每次40 mL，分离出有机相后，水相合并后用二氯甲烷萃取两次，每次20 mL，合并有机相用3g无水硫酸钠干燥20 min，干燥后的有机相通过减压蒸馏回收溶剂后得到粗产物，用200-300目硅胶柱层析分离，所用洗脱剂为10:1的石油醚和乙酸乙酯，收集第四带为目标产物溶液，减压蒸馏回收溶剂，得到546 mg淡黄色固体，为化合物1，产率为69%。
(2)将40 mg化合物1溶解于3 mL二氯甲烷中，加入1470 mg 17%的三溴化硼的二氯甲烷溶液，在氮气的保护下，-10 ℃条件下搅拌反应1 h，将温度升高到室温，在该条件下搅拌反应3 h。反应结束后用2 mL饱和氯化钠水溶液猝灭反应液，用10 mL二氯甲烷稀释猝灭后的反应液并转移到分液漏斗中，有机相用饱和氯化铵水溶液洗涤两次，每次15 mL，分离出有机相后，水相合并后用15 mL二氯甲烷萃取一次，合并有机相用1.5 g无水硫酸钠干燥20 min，干燥后的有机相通过减压蒸馏回收溶剂后得到粗产物，用200-300目硅胶柱层析分离，所用洗脱剂为50:1的二氯甲烷和甲醇，收集第三带为目标产物溶液，减压蒸馏回收溶剂，得到32 mg黄绿色固体，为化合物2，产率为87%。
Claims (6)
1.一种羟基取代的硫杂芴的制备方法，其特征在于：目标产物具有式2所示结构：
2.一种羟基取代的硫杂芴的制备方法，其特征在于：化合物1的制备方法中反应物的质量比为，2,8-二溴硫杂芴：4-[N,N-二(4-二甲氧基苯基)胺基]苯硼酸频哪醇酯：四(三苯基膦)钯：碳酸钠 = 1：2.646：0.608：0.930。
3.一种羟基取代的硫杂芴的制备方法，其特征在于：化合物1的制备方法中反应温度为95 ℃。
4.一种羟基取代的硫杂芴的制备方法，其特征在于：化合物1的制备方法中反应时间为16 h。
5.一种羟基取代的硫杂芴的制备方法，其特征在于：化合物2的制备方法中反应物的质量比为，化合物1：17%的三溴化硼二氯甲烷溶液 = 1：36.750。
6.一种羟基取代的硫杂芴的制备方法，其特征在于：化合物2的制备方法中反应条件为，先在-10 ℃反应1 h，再升温至室温反应3 h。
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2005112765A (ja) * | 2003-10-07 | 2005-04-28 | Mitsui Chemicals Inc | 複素環化合物および該化合物を含有する有機電界発光素子 |
| JP2006248984A (ja) * | 2005-03-10 | 2006-09-21 | Univ Nagoya | ９−置換フルオレン誘導体及びその製造方法 |
| CN109564972A (zh) * | 2017-03-09 | 2019-04-02 | 株式会社Lg化学 | 有机发光元件 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2005112765A (ja) * | 2003-10-07 | 2005-04-28 | Mitsui Chemicals Inc | 複素環化合物および該化合物を含有する有機電界発光素子 |
| JP2006248984A (ja) * | 2005-03-10 | 2006-09-21 | Univ Nagoya | ９−置換フルオレン誘導体及びその製造方法 |
| CN109564972A (zh) * | 2017-03-09 | 2019-04-02 | 株式会社Lg化学 | 有机发光元件 |
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