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Bridge-Driven Aggregation control in Dibenzofulvene-Naphthalimide Based Donor−Bridge−Acceptor Systems:  Enabling Fluorescence Enhancement, Blue to Red Emission and Solvatochromism
Materials Chemistry Frontiers ( IF 6.0 ) Pub Date : 2017-09-08 00:00:00 , DOI: 10.1039/c7qm00357a
Peddaboodi Gopikrishna 1, 2, 3, 4 , Laxmi Raman Adil 2, 3, 4, 5 , Parameswar Krishnan Iyer 1, 2, 3, 4, 5
Affiliation  

Four novel 1,8-naphthalimide (NC) and mono-substituted dibenzofulvene (DBF) based structures have been designed and successfully synthesized. Two luminogens were substituted by a thiophene bridge (DT1NC and DT2NC) while the two other luminogens were substituted by a phenyl bridge (DP1NC and DP2NC) between NC and DBF units. This minor structural modification crafts striking changes in the photophysical behavior. DT1NC and DT2NC displayed aggregation induced emission enhancement (AIEE) behavior. They also showed orange and red emission (575 nm and 602 nm) respectively with large bathochromic shifts (35 nm and 112 nm) and high quantum yields (84.10% and 65.65%) in the aggregated state due to ladder type J-aggregation. DP1NC exhibited weak AIEE behavior in blue region while DP2NC showed AIE inactive nature due to the strong C-H•••π intermolecular interactions. All luminogens showed positive solvatochromism caused by intramolecular charge transfer (ICT). The DT2NC and DP2NC luminogens were substituted with two bromine atoms at 2,7 positions of the DBF moiety, but unexpectedly only the DT2NC showed strong heavy atom effect. Theoretical and experimental HOMO and LUMO energy levels were estimated by the density functional theory and cyclic voltammetry respectively. All luminogens displayed excellent thermal stabilities and good morphological behavior.

中文翻译:

基于二苯并富勒萘-萘二甲酰亚胺的供体-桥-受体系统中的桥驱动聚集控制:启用荧光增强,蓝到红发射和溶剂变色。

已经设计并成功合成了四种新颖的1,8-萘二甲酰亚胺(NC)和单取代的二苯并富勒烯(DBF)基结构。NC和DBF单元之间的两个发光剂被噻吩桥(DT1NC和DT2NC)取代,而其他两个发光剂被苯基桥(DP1NC和DP2NC)取代。这种微小的结构改变使光物理行为发生了显着变化。DT1NC和DT2NC显示聚集诱导的发射增强(AIEE)行为。它们还显示出橙色和红色发射(575 nm和602 nm),分别由于梯形J聚集而在聚集状态下具有大的红移(35 nm和112 nm)和高量子产率(84.10%和65.65%)。DP1NC在蓝色区域表现出较弱的AIEE行为,而DP2NC由于强烈的CH•••π分子间相互作用而表现出AIE失活的性质。所有的发光剂均显示出由分子内电荷转移(ICT)引起的正溶剂溶变色现象。DT2NC和DP2NC发光剂在DBF部分的2,7位被两个溴原子取代,但是出乎意料的是,只有DT2NC表现出很强的重原子作用。理论和实验HOMO和LUMO能级分别通过密度泛函理论和循环伏安法估算。所有发光剂均表现出优异的热稳定性和良好的形态学行为。但出乎意料的是,只有DT2NC才显示出强大的重原子效应。理论和实验HOMO和LUMO能级分别通过密度泛函理论和循环伏安法估算。所有发光剂均表现出优异的热稳定性和良好的形态学行为。但出乎意料的是,只有DT2NC才显示出强大的重原子效应。理论和实验HOMO和LUMO能级分别通过密度泛函理论和循环伏安法估算。所有发光剂均表现出优异的热稳定性和良好的形态学行为。
更新日期:2017-09-08
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