Asymmetric Difluoroboron Quinazolinone-Pyridine Dyes with Large Stokes Shift: High Emission Efficiencies Both in Solution and in the Solid State
Asymmetric Difluoroboron Quinazolinone-Pyridine Dyes with Large Stokes Shift: High Emission Efficiencies Both in Solution and in the Solid State
复制标题
具有大斯托克斯位移的不对称二氟硼喹唑啉酮-吡啶染料：溶液和固态均具有高发射效率
DOI：
10.1002/chem.201803428
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Song Zhibin
中科院分区：
文献类型：
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作者：
Zhou Jia;Liu Lu;Pan Ying;Zhu Qiaoyu;Lu Yajie;Wei Jiacheng;Luo Kang;Fu Yang;Zhong Cheng;Peng Yiyuan;Song Zhibin
设计并合成了二氟喹唑啉酮吡啶硼（BODIQPy）及其取代衍生物。这些不对称 BODIQPy 在溶液（高达 0.99）和固态（高达 0.60）中均实现了强发射和高荧光量子产率。对于6-卤素取代的BODIQPys，由于BODIQPycore的强吸电子能力，溶液中溴和碘的重原子效应被抑制。结果，6-碘取代的BODIQPy在二氯甲烷和四氢呋喃中显示出不寻常的荧光量子产率（>0.70）。在固态下，不对称结构诱导出独特的二聚体结构，并且还观察到有效的发光。羰基氧与溴或碘之间形成卤素键调节堆积模式并增强分子间相互作用，导致荧光量子产率下降。此外，这些不对称BODIQPy 也实现了较大的斯托克斯位移。
Boron difluoroquinazolinone‐pyridine (BODIQPy) and substituted derivatives have been designed and synthesized. Strong emission with high fluorescence quantum yield both in solution (up to 0.99) and in solid state (up to 0.60) was achieved in these asymmetricBODIQPys. For 6‐halogen substitutedBODIQPys, the heavy atomic effect of bromine and iodine was suppressed in solution due to the strong electron‐withdrawing ability of theBODIQPycore. As a result, 6‐iodine substitutedBODIQPyshows the unusual fluorescence quantum yields (>0.70) in dichloromethane and tetrahydrofuran. In the solid state, the asymmetric structure induced a unique dimeric structure, and efficient luminescence was also observed. The formation of halogen bonds between carbonyl oxygen and bromine or iodine regulated the stacking mode and enhanced intermolecular interaction, resulting in a decline in the fluorescence quantum yield. In addition, a large Stokes shift was also achieved in these asymmetricBODIQPys.