Systematic Modulation of the Fluorescence Brightness in Boron-Dipyrromethene (BODIPY)-Tagged N-Heterocyclic Carbene (NHC)-Gold-Thiolates

Halter Oliver; Vasiuta Roman; Fernandez Israel; Plenio Herbert

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Systematic Modulation of the Fluorescence Brightness in Boron-Dipyrromethene (BODIPY)-Tagged N-Heterocyclic Carbene (NHC)-Gold-Thiolates

机译：硼-二吡咯亚甲基（BODIPY）标记的N-杂环卡宾（NHC）-金-硫醇盐的荧光亮度的系统调节

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Five different highly fluorescent boron-dipyrromethene (BODIPY)-tagged N-heterocyclic carbene NHC-gold halide complexes were synthesized. The substitution of the halogeno ligand by 4-substituted aryl thiolates leads to a decrease in the brightness of the complexes. This decrease depends on the electronic nature of the thiols, being most pronounced with highly electron-rich thiols (4-R=NMe2). The brightness of the gold thiolates also depends on the distance between the sulfur atom and the BODIPY moiety. The systematic variation of the electron density of [(NHC-bodipy)Au(SC6H4R)] (via different R groups) enables the systematic variation of the fluorescence brightness of an appended BODIPY fluorophore. Based on this and supported by DFT calculations, a photoinduced electron-transfer quenching appears to be the dominant mechanism controlling the brightness of the appended BODIPY dye.

机译：合成了五种不同的高荧光硼二吡咯亚甲基（BODIPY）标签的N-杂环卡宾NHC-金卤化物配合物。 4-取代的芳基硫醇盐对卤代配体的取代导致配合物的亮度降低。这种降低取决于硫醇的电子性质，其中高度富电子的硫醇（4-R = NMe2）最明显。硫醇金的亮度还取决于硫原子与BODIPY部分之间的距离。 [（NHC-bodipy）Au（SC6H4R）]的电子密度的系统变化（通过不同的R基团）可以使所附加的BODIPY荧光团的荧光亮度发生系统变化。基于此并得到DFT计算的支持，光诱导的电子转移猝灭似乎是控制附加的BODIPY染料亮度的主要机理。

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《Chemistry: A European journal》 |2016年第50期|共7页
作者
Halter Oliver; Vasiuta Roman; Fernandez Israel; Plenio Herbert;
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正文语种 eng
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BODIPY; gold; fluorescence; ligand substitution; photoinduced electron transfer;

机译：BODIPY;金;荧光;配体取代;光致电子转移;

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1. Systematic Modulation of the Fluorescence Brightness in Boron-Dipyrromethene (BODIPY)-Tagged N-Heterocyclic Carbene (NHC)-Gold-Thiolates [J] . Halter Oliver, Vasiuta Roman, Fernandez Israel, Chemistry: A European journal . 2016,第50期

机译：硼-二吡咯亚甲基（BODIPY）标记的N-杂环卡宾（NHC）-金-硫醇盐的荧光亮度的系统调节
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机译：（A / N-NHC）PDX2（吡啶）和（A / N-NHC）（2）PDX2（X = I，CL）异常熔融 - 双环咪唑的型复合物（A / N-NHC）和（A / N-NHC）（2）PDX2（X = I，CL）[1,2-A]吡啶基正杂胺基于苏苏 - 宫达偶联反应中的正杂环基石（A-NHC）和正常的咪唑基N-杂环（N-NHC）配体
3. Porphyrins Fused to N-Heterocyclic Carbenes (NHCs): Modulation of the Electronic and Catalytic Properties of NHCs by the Central Metal of the Porphyrin [J] . Jean-Fran?ois Lefebvre, Mamadou Lo, Jean-Paul Gisselbrecht, Chemistry: A European journal . 2013,第46期

机译：卟啉与N-杂环卡宾（NHCs）融合：卟啉中心金属对NHC的电子和催化性质的调控
4. Synthesis of Nickel(II) N-Heterocyclic Carbene (NHC) Complexes, Catalyzing Cross-coupling Reactions [C] . Kouki Matsubara, Keita Ueno Symposium on Organometallic Chemistry . 2006

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5. Macrocyclic N-Heterocyclic Carbenes (NHC) for Size-Selective Nucleophilic Catalysis and Olefin Metathesis [D] . Zhang, Yutong. 2021

机译：大规模的N-杂环碳酸（NHC）用于大小选择性亲核催碱和烯烃复分解
6. Reactivity of Cyclic (Alkyl)(amino)carbenes (CAACs) and Bis(amino)cyclopropenylidenes (BACs) with Heteroallenes: Comparisons with their N-heterocyclic Carbene (NHCs) Counterparts [O] . Glenn Kuchenbeiser, Michele Soleilhavoup, Bruno Donnadieu, -1

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7. Computation Provides Chemical Insight into the Diverse Hydride NMR Chemical Shifts of [Ru(NHC)4(L)H]0/+ Species (NHC = N-heterocyclic carbene; L = vacant, H2, N2, CO, MeCN, O2, P4, SO2, H-, F- and Cl-) and their [Ru(R2PCH2CH2PR2)2(L)H]+ Congeners [O] . Haller, L J L, Mas-Marza, Elena, Cybulski, Mateusz K, 2017

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Systematic Modulation of the Fluorescence Brightness in Boron-Dipyrromethene (BODIPY)-Tagged N-Heterocyclic Carbene (NHC)-Gold-Thiolates

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