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The Dual‐State Luminescent Mechanism of 2,3,4,5‐Tetraphenyl‐1H‐pyrrole
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-08-28 , DOI: 10.1002/chem.201803080 Yunxiang Lei 1 , Qianwei Liu 1 , Lichao Dong 1 , Zhengxu Cai 1 , Jianbing Shi 1 , Junge Zhi 2 , Bin Tong 1 , Yuping Dong 1
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-08-28 , DOI: 10.1002/chem.201803080 Yunxiang Lei 1 , Qianwei Liu 1 , Lichao Dong 1 , Zhengxu Cai 1 , Jianbing Shi 1 , Junge Zhi 2 , Bin Tong 1 , Yuping Dong 1
Affiliation
2,3,4,5‐Tetraphenyl‐1H‐pyrrole (TePP) was synthesized by a simple one‐step reaction. The compound showed a balanced emission in both the solution and solid state with the absolute quantum yield of ΦF/THF=65.6 % and ΦF/solid=74.3 %, respectively. Temperature and viscosity variation measurements demonstrated that the phenyl group at the 1‐position (N‐position) of the pyrrole core can act as a rotor in pyrrole‐based molecules, which can consume the excited energy and reduce the molecular emission in solution. TePP without the phenyl group at the 1‐position can effectively enhance the emission in solution. Single‐crystal analysis showed that the phenyl groups at the 2,5‐positions of pyrrole extend the molecular conjugation and lock the conformation. The phenyl groups at the 3,4‐positions with a twisted conformation prevent their molecules from close packing and are helpful for aggregated emission. A delicate balance between the twisting conformation and rigid conjugation takes advantage of both ACQ and AIE luminogens. The strategy can tune the AIE, ACQ, or solution and solid dual‐state emission properties of pyrrole‐based molecules by simply altering the position of phenyl groups, which provides a great opportunity to explore the luminescent mechanism in greater detail and to facilitate practical applications.
中文翻译:
2,3,4,5-四苯基-1H-吡咯的双态发光机理
通过简单的一步反应合成了2,3,4,5-四苯-1 H-吡咯(TePP)。该化合物在溶液和固态下均显示出平衡的发射,其绝对量子产率分别为ΦF / THF = 65.6%和ΦF / solid = 74.3%。温度和粘度变化测量结果表明,吡咯核芯1位(N位)处的苯基可以作为吡咯基分子的转子,从而消耗激发能并减少溶液中的分子发射。聚四氟乙烯如果在1位上没有苯基,则可以有效地提高溶液中的发射率。单晶分析表明,吡咯的2,5-位上的苯基扩展了分子共轭并锁定了构象。具有扭曲构象的3,4位上的苯基可防止其分子紧密堆积,并有助于聚集发射。扭转构象和刚性共轭之间的微妙平衡利用了ACQ和AIE发光原。该策略可通过简单地改变苯基的位置来调整吡咯基分子的AIE,ACQ或溶液和固态双态发射特性,这为更详细地探索发光机理和促进实际应用提供了巨大的机会。
更新日期:2018-08-28
中文翻译:
2,3,4,5-四苯基-1H-吡咯的双态发光机理
通过简单的一步反应合成了2,3,4,5-四苯-1 H-吡咯(TePP)。该化合物在溶液和固态下均显示出平衡的发射,其绝对量子产率分别为ΦF / THF = 65.6%和ΦF / solid = 74.3%。温度和粘度变化测量结果表明,吡咯核芯1位(N位)处的苯基可以作为吡咯基分子的转子,从而消耗激发能并减少溶液中的分子发射。聚四氟乙烯如果在1位上没有苯基,则可以有效地提高溶液中的发射率。单晶分析表明,吡咯的2,5-位上的苯基扩展了分子共轭并锁定了构象。具有扭曲构象的3,4位上的苯基可防止其分子紧密堆积,并有助于聚集发射。扭转构象和刚性共轭之间的微妙平衡利用了ACQ和AIE发光原。该策略可通过简单地改变苯基的位置来调整吡咯基分子的AIE,ACQ或溶液和固态双态发射特性,这为更详细地探索发光机理和促进实际应用提供了巨大的机会。