Managing nucleophilic addition reactions to tune the physical properties of 2-substituted pentamethylBODIPY derivatives

Sritharan, S. R.; Hussein, Burhan A.; Machin, Devin D.; El-Aooiti, Malek; Adjei, Jeanette A.; Singh, Jagriti; Pau, Jeffrey; Dhindsa, Jasveer S.; Lough, Alan J.; Koivisto, Bryan D.

doi:10.1039/c6ra28114a

“…α-substituted ferrocenyl BODIPY dyads and triads 58,59 In a study by Zatsikha et al, donor-acceptor dyads with ferrocene installed on the α-position to BODIPY through a vinyl bridge were examined ( heated to 150°C, the compound decomposed after 5 h. 61 Sritharan et al, synthesized 3.24 using nucleophilic addition reaction to form a Schiff base bridged dyad. 62 The UV-Vis absorption profile shows a π-π* transition for BODIPY at 511 nm and a MLCT absorption band around 560 nm owing to the ferrocene unit. 62 Dyad 3.24 was also found to be unstable in solution under ambient conditions over time.…”

Section: Meso-substituted Methylated Ferrocenyl Bodipymentioning

confidence: 98%

Mixed Metal-Organic Dyes With Dual Electrophores: Designing More Robust Dyes for Light-Harvesting Applications

Huynh¹

2021

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Donor-π-spacer-acceptor architectures are a favourable motif in the design of dyes for light harvesting applications. Organic compounds offer cost-effectiveness and synthetic design versatility, while inorganic compounds possess long term redox stability and wide range for absorption. Uniting both types of molecules allows utilization of these properties. Several projects were undertaken with the theme of a hybrid dye system and study of their redox stability. Chapter 1 gives a brief overview of the inorganic and organic compounds that paved the research in DSSC dyes. Chapter 2 details a review on copper(I) dyes in the literature and preliminary synthesis towards a D-π-A templated copper(I) dye. Chapter 3 looks into the robust potential of novel BODIPY dyes that utilize ferrocene as an electron rich donor. Chapter 4 represents a series of BODIPY-redox active donor dyads, the study of their redox stability provide insight on the decomposition pathway of these conjugates.

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“…62 The UV-Vis absorption profile shows a π-π* transition for BODIPY at 511 nm and a MLCT absorption band around 560 nm owing to the ferrocene unit. 62 Dyad 3.24 was also found to be unstable in solution under ambient conditions over time. 53,62 As of yet, there are only two reports of methylated BODIPY dyads with ferrocene appended at the β-position.…”

Section: Meso-substituted Methylated Ferrocenyl Bodipymentioning

confidence: 98%

“…62 Dyad 3.24 was also found to be unstable in solution under ambient conditions over time. 53,62 As of yet, there are only two reports of methylated BODIPY dyads with ferrocene appended at the β-position. There exists a series of non-methylated BODIPY with α-substituted ferrocene bound through an ethynyl linker, however no other physico-chemical properties were studied.…”

Section: Meso-substituted Methylated Ferrocenyl Bodipymentioning

confidence: 99%

Mixed Metal-Organic Dyes With Dual Electrophores: Designing More Robust Dyes for Light-Harvesting Applications

Huynh¹

2021

Preprint

0

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Donor-π-spacer-acceptor architectures are a favourable motif in the design of dyes for light harvesting applications. Organic compounds offer cost-effectiveness and synthetic design versatility, while inorganic compounds possess long term redox stability and wide range for absorption. Uniting both types of molecules allows utilization of these properties. Several projects were undertaken with the theme of a hybrid dye system and study of their redox stability. Chapter 1 gives a brief overview of the inorganic and organic compounds that paved the research in DSSC dyes. Chapter 2 details a review on copper(I) dyes in the literature and preliminary synthesis towards a D-π-A templated copper(I) dye. Chapter 3 looks into the robust potential of novel BODIPY dyes that utilize ferrocene as an electron rich donor. Chapter 4 represents a series of BODIPY-redox active donor dyads, the study of their redox stability provide insight on the decomposition pathway of these conjugates.

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“…值得注意的是, BODIPY α 位的醛基和一级胺发生 Schiff 反应的例子鲜有报道, 这类 Schiff 反应只在 BODIPY 的 β 位有过报道 [54] . 另外, 使用 BODIPY α 位醛基做 Knoevenagel 反应的例子也很少见.…”

Section: α 位酰化的 Bodipy 的反应unclassified

Progress in the Synthesis of Boron Dipyrromethene (BODIPY) Fluorescent Dyes

Liu¹,

Teng²,

Niu³

et al. 2022

Chinese Journal of Organic Chemistry

3

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Boron dipyrromethene (BODIPY) dyes are widely used in the fields of life sciences, chemical analysis and optoelectronic materials due to its excellent photophysical properties, favorable biocompatibility, facile synthesis and modification etc. The synthesis and derivative strategies of BODIPY provide the basis for its wide application and have attracted great attention from researchers. In this review, the modification strategies for different reaction positions of BODIPY have been discussed, and Pd-catalyzed cross-coupling reactions and oxidative coupling reactions about BODIPY are discussed individually. Finallly, the development of this field is prospected. Keywords boron dipyrromethene (BODIPY); fluorescent dyes; synthesis; functional modification 有机荧光染料在电致发光、荧光探针、生物成像、防伪等领域有着广泛的应用. 常见的有机荧光染料包括氟硼二吡咯(BODIPY) [1][2] 、荧光素 [3][4] 、香豆素 [5] 、罗丹明 [6] 、菁染料 [7] 、酰亚胺类 [8][9][10] 和硝基苯并恶二唑(NBD) 类 [11] 等. 其中, BODIPY 类有机荧光染料具有优异的光物理性质, 如摩尔消光系数大、荧光量子产率高、吸收和发射半峰宽窄、光物理性能受外界环境(比如溶剂、 pH 等)影响小等. 更重要的是, BODIPY 具有良好的生物

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Managing nucleophilic addition reactions to tune the physical properties of 2-substituted pentamethylBODIPY derivatives

Abstract: A structure–property study using a new approach to electronically desymmetrize the BODIFY core.

Cited by 9 publications

References 18 publications

Mixed Metal-Organic Dyes With Dual Electrophores: Designing More Robust Dyes for Light-Harvesting Applications

Mixed Metal-Organic Dyes With Dual Electrophores: Designing More Robust Dyes for Light-Harvesting Applications

Mixed Metal-Organic Dyes With Dual Electrophores: Designing More Robust Dyes for Light-Harvesting Applications

Progress in the Synthesis of Boron Dipyrromethene (BODIPY) Fluorescent Dyes

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