Phenanthro[9,10-<i>d</i>]imidazole-quinoline Boron Difluoride Dyes with Solid-State Red Fluorescence

Li, Weiling; Lin, Weiying; Wang, Jiaoliang; Guan, Bin

doi:10.1021/ol400605x

Cited by 105 publications

(70 citation statements)

References 29 publications

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“…The excellent photophysical features of the BODIPY scaffold in bioimaging, encouraged us to explore the generation of novel BODIPY fluorophores arising from α‐pyridyl‐GBBR adducts. Remarkably, model GBBR compound 17 reacted with BF 3 to selectively render complex 18 a (Figure B), which displays a BF 2 bridge linking the imino group and the pyridine nitrogen, suggesting that the formation of the 5‐membered ring is faster than the conventional 6‐membered BODIPY cycle . Analogously, the BODIPY‐like compound 18 b was obtained from the double GBBR adduct 5 d (Figure C).…”

Section: Resultsmentioning

confidence: 97%

Multiple Multicomponent Reactions: Unexplored Substrates, Selective Processes, and Versatile Chemotypes in Biomedicine

Ghashghaei

Caputo

Sintes

et al. 2018

Chemistry A European J

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Multiple multicomponent reactions rapidly assemble complex structures. Despite being very productive, the lack of selectivity and the reduced number of viable transformations restrict their general application in synthesis. Hereby, we describe a rationale for a selective version of these processes based in the preferential generation of intermediates which are less reactive than the initial substrates. In this way, applying the Groebke-Blackburn-Bienaymé reaction on a range of α-polyamino-polyazines, we prepared a family compact heterocyclic scaffolds with relevant applications in medicinal and biological chemistry (live cell imaging probes, selective binders for DNA quadruplexes, and antiviral agents against human adenoviruses). The approach has general character and yields complex molecular targets in a selective, tunable and direct manner.

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Section: Resultsmentioning

confidence: 97%

Multiple Multicomponent Reactions: Unexplored Substrates, Selective Processes, and Versatile Chemotypes in Biomedicine

Ghashghaei

Caputo

Sintes

et al. 2018

Chemistry A European J

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“…Due to the poor solubility of the ligands 5-8 in toluene and other common organic solvents (see Supporting Information), a much longer reaction time was required to convert the chelating ligands into boron-cored dyes by comparison to the similar reactions reported. [11] The resultant complexes 1-4 exhibited good chemical stability even when exposed to air for several months.…”

Section: Resultsmentioning

confidence: 99%

“…[11] The mixture was heated to 80 8C, and during the heating process, the color of the solution changed from red to blue. The reaction mixture was further stirred for 12 h at 80 8C.…”

Section: Synthesesmentioning

confidence: 99%

Geometric and Electronic Structures of Boron(III)‐Cored Dyes Tailored by Incorporation of Heteroatoms into Ligands

Sun

Zhang

Wang

et al. 2015

Chemistry An Asian Journal

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Complexation of a boron atom with a series of bidentate heterocyclic ligands successfully gives rise to corresponding BF2-chelated heteroarenes, which could be considered as novel boron(III)-cored dyes. These dye molecules exhibit planar structures and expanded π-conjugated backbones due to the locked conformation with a boron center. The geometric and electronic structures of these BF2 complexes can be tailored by embedding heteroatoms in the unique modes to form positional isomer and isoelectronic structures. The structure-property relationship is further elucidated by studying the photophysical properties, electrochemical behavior and quantum-chemical calculations.

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“…Existing strategies to lower the symmetry of the parent dipyrromethene ligand system (Figure ) involve: 1) replacing the amido N‐donor with anionic imidazolate, indolate, carbazolate, anilide, O‐donor, or C‐donor units; 2) replacing the imino N‐donor with charge‐neutral pyridine, quinoline, pyrimidine, thiazole, or imine groups.…”

Section: Introductionmentioning

confidence: 97%

BOIMPY: Fluorescent Boron Complexes with Tunable and Environment‐Responsive Light‐Emitting Properties

Lee

Park

Cho

et al. 2016

Chemistry A European J

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A series of air-stable boron complexes 1-5 were prepared by using N-aryl iminopyrrolide ligands. Designed as minimalist structural mimics of the privileged BODIPY motif, these new BOIMPY (BOron complexes of IMinoPYrrolide ligands) fluorophores feature low molecular symmetry that promotes emission from CT-type excited states with large Stokes shifts and little self-quenching. Through comparative studies on the homologous set of compounds 1-4, we have confirmed that a delicate interplay between conformational twisting and donor-acceptor interaction dictates the mechanism of de-excitation, which responds sensitively to solvent polarity as well as protonation states. Over a wide visible spectral range, the structure-dependent light-emitting properties of BOIMPY molecules are well manifested, even in the solid-state. In order to exploit the environment-sensitive nature of CT-type emission, the BOIMPY motif was elaborated further into a bioprobe molecule 5. Live-cell fluorescence imaging studies have established that 5 is localized exclusively at lipid droplets to produce well-resolved staining patterns without affecting cell viability. These findings promise future elaboration of BOIMPY-based functional molecules for applications in biological imaging, chemical sensing, and molecular switching.

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Phenanthro[9,10-d]imidazole-quinoline Boron Difluoride Dyes with Solid-State Red Fluorescence

Cited by 105 publications

References 29 publications

Multiple Multicomponent Reactions: Unexplored Substrates, Selective Processes, and Versatile Chemotypes in Biomedicine

Multiple Multicomponent Reactions: Unexplored Substrates, Selective Processes, and Versatile Chemotypes in Biomedicine

Geometric and Electronic Structures of Boron(III)‐Cored Dyes Tailored by Incorporation of Heteroatoms into Ligands

BOIMPY: Fluorescent Boron Complexes with Tunable and Environment‐Responsive Light‐Emitting Properties

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