Electrogenerated Chemiluminescence of a BODIPY Derivative with Extended Conjugation

Electrogenerated Chemiluminescence of a BODIPY Derivative with Extended Conjugation
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DOI:
10.1002/slct.201702449
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发表时间:
2017-11
期刊:
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通讯作者:
R. Ishimatsu;Hirosato Shintaku;C. Adachi;K. Nakano;T. Imato
R. Ishimatsu;Hirosato Shintaku;C. Adachi;K. Nakano;T. Imato
中科院分区:
其他
文献类型:
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作者:
R. Ishimatsu;Hirosato Shintaku;C. Adachi;K. Nakano;T. Imato

文献摘要

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研究了硼二吡咯甲烷(BODIPY)衍生物2,8-双(4-异丙基苯基)-二呋喃并[2,3-B][3,2-g]-5,5-二氟-5-硼-3a,4a-二氮杂-均-引达省(图1)的电化学性质和电致化学发光(ECL)。衍生物1以三丙胺(TPA)为共反应物,在650 ~ 800 nm范围内发射出电致发光. 在循环伏安图中,衍生物1显示可逆的氧化波,而还原波是不可逆的。能量上,三重态-三重态湮灭可能是通过衍生物1的自由基阴离子和阳离子的离子湮灭发射ECL的主要途径,而衍生物1的最低激发单重态直接由TPA产生。最大ECL波长(0.01 mM时为670 nm)随着衍生物1浓度的增加而红移,因为小斯托克斯位移(≤ 10 nm)导致自吸收。   与Ru(bpy)2+/TPA体系相比,衍生物1的相对ECL效率为0.13。
The electrochemical properties and electrogenerated chemiluminescence (ECL) of a borondipyrromethane (BODIPY) derivative, 2,8‐bis(4‐isopropylphenyl)‐difuro[2, 3‐b][3, 2‐g]‐5,5‐difluoro‐5‐bora‐3a,4a‐diaza‐s‐indacene (Derivative 1, Figure 1) are described. Derivative 1 emitted ECL in the range of 650∼800 nm by using tripropylamine (TPA) as a coreactant. In the cyclic voltammogram, Derivative 1 showed a reversible oxidation wave, whereas the reduction wave was irreversible. Energetically, it is likely that triplet‐triplet annihilation is the main pathway to emit ECL through the ion annihilation of the radical anions and cations of Derivative 1 whereas the lowest excited singlet state of Derivative 1 is directly produced with TPA. The maximum ECL wavelengths (670 nm at 0.01 mM) were red‐shifted with increasing the concentration of Derivative 1 because of the self‐absorption resulted from a small Stokes shift (∼10 nm). Relative ECL efficiency of Derivative 1 was 0.13 compared to that of a Ru(bpy)2+/TPA system.