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1,2,5-三苯基吡咯的合成及其聚集程度对发光强度的影响
  • ISSN号:1000-0593
  • 期刊名称:《光谱学与光谱分析》
  • 时间:0
  • 分类:O626.1[理学—有机化学;理学—化学]
  • 作者机构:[1]北京理工大学材料科学与工程学院,北京100081, [2]北京理工大学理学院,北京100081
  • 相关基金:国家自然科学基金项目(20634020)资助
中文摘要:

采用Schulte-Reisch方法,在氯化亚铜催化下,由1,4-二苯基丁二炔与苯胺反应成功制备了1,2,5-三苯基吡咯(TPP)。通过将溶液反应改进为本体反应,不仅提高了收率,而且降低了反应温度,缩短了反应时间。当水的含量在THF-水混合溶剂中低于60%时,因TPP没有产生聚集,其荧光强度基本没有发生变化;但水含量增加到70%时,因聚集紧密程度较低,π—π堆积作用诱发非辐射能量转移,使荧光强度被猝灭;而当水的含量超过80%以上时,TPP呈现高紧密聚集,使分子内旋转受到限制,降低了非辐射能量转移,使发光得到增强。由于乙腈与TPP之间所形成的较强电荷转移相互作用影响了聚集紧密程度,没有呈现高聚集诱导发光增强性质。

英文摘要:

1,2,5-triphenylpyrrole (TPP) was firstly prepared by the Schulte-Reisch reaction of 1,4-diphenylbuta-1,3-diyne with aniline catalyzed by copper chloride. Compared to solution reaction in DMF as solvent, the bulk reaction modified in this paper not only increased the yield and reduced the reaction temperature, but also shortend the reaction time. The π-π stacking inter action and the restriction of intramolecular rotation are were involved at the same time when TPP was aggregated in the THF-- water mixtures. When the water volume fraction was under 60 %, the PL intensity of TPP was independent on the water fraction in THF:water mixture. When the water fraction was added to 70%, which induced the non-tight aggregation of TPP, the strong π-π stacking interaction toned the nonradiative deactivation process and led to quenching the fluorescence of TPP; if the water fraction was further increased to 80%, which induced the tight aggregation of TPP, the restriction of intramolecular rotation was, however, preponderant over π-π stacking interaction. Thus the nonradiative channel was blocked and the photolumineseence intensity of TPP was enhanced. The compact degree of aggregation was influenced by aeetonitrile solvent due to the charge transfer interaction between TPP and acetonitrile. The aggregation-induced emission enhancement of TPP in THF-water mixture disappeared in acetonitrile-water mixture.

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期刊信息
  • 《光谱学与光谱分析》
  • 中国科技核心期刊
  • 主管单位:中国科学技术协会
  • 主办单位:中国光学学会
  • 主编:高松
  • 地址:北京海淀区魏公村学院南路76号
  • 邮编:100081
  • 邮箱:chngpxygpfx@vip.sina.com
  • 电话:010-62181070
  • 国际标准刊号:ISSN:1000-0593
  • 国内统一刊号:ISSN:11-2200/O4
  • 邮发代号:82-68
  • 获奖情况:
  • 1992年北京出版局编辑质量奖,1996年中国科协优秀科技期刊奖,1997-2000获中国科协择优支持基础性高科技学术期刊奖
  • 国内外数据库收录:
  • 俄罗斯文摘杂志,美国化学文摘(网络版),荷兰文摘与引文数据库,美国工程索引,美国生物医学检索系统,美国科学引文索引(扩展库),英国科学文摘数据库,日本日本科学技术振兴机构数据库,中国中国科技核心期刊,中国北大核心期刊(2004版),中国北大核心期刊(2008版),中国北大核心期刊(2011版),中国北大核心期刊(2014版),英国英国皇家化学学会文摘,中国北大核心期刊(2000版)
  • 被引量:40642