Two‐Step Synthetic Route toward Asymmetric and Symmetric Boron Dipyrromethenes: Synthesis, Optical Properties, and Electrochemistry

Swavey, Shawn; Coladipietro, Michael; Burbayea, Aliah; Krause, Jeanette A.

doi:10.1002/ejoc.201600787

Cited by 19 publications

(13 citation statements)

References 64 publications

(73 reference statements)

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“…In light of the recent report on the two-step synthetic route of highly conjugated BODIPY dyes 26 we have attempted to extend this synthetic route. By heating naphtha[1,2-c]pyrrole and 1-pyrenecarboxaldehyde at 80 C for 15 min followed by chromatography on silica gel, the red dipyrrin was obtained.…”

Section: Synthesismentioning

confidence: 99%

“…The luminescence quantum efficiency for 5 was determined previously to be 0.9. 26 Typically BODIPY dyes with emission maxima greater than 600 nm exhibit quantum efficiencies well below unity. Notably, the quantum efficiency of 8 is 0.8, considerably higher than that observed for similar dyes with emission also peaking near 650 nm.…”

Section: Spectroscopic Propertiesmentioning

confidence: 99%

“…Rurack et al has achieved luminescence quantum efficiencies near unity with absorption wavelengths between 621 nm and 642 nm from phenanthrene-fused BODIPY dyes with various mesosubstituents. 25 We have recently described a two-step route toward BODIPY dyes 26 in which formation of the dipyrrin was accomplished in the absence of solvent. Using naphthyl-pyrrole and a variety of aromatic aldehydes, a series of new BODIPY dyes were generated with long-wavelength absorption properties ranging from ca.…”

Section: Introductionmentioning

confidence: 99%

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Tuning the photophysical properties of BODIPY dyes through extended aromatic pyrroles

et al. 2017

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Section: Synthesismentioning

confidence: 99%

Section: Spectroscopic Propertiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Tuning the photophysical properties of BODIPY dyes through extended aromatic pyrroles

et al. 2017

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“…However, it is important to emphasize that introducing new functional groups is not without challenges, especially in cases where additional molecular asymmetry is introduced [6] . Recently, nitrosyl monosubstitution of BODIPYs was reported in the literature, [7] and this direct nitrosation opens up several avenues for the development of new fluorescent probes, for different applications.…”

Section: Introductionmentioning

confidence: 99%

“…Electrochemical studies are useful in understanding the redox properties of these materials and in evaluating structure stability relations for the radical ions, cation or anion ones [11–12] . Coupled with spectroscopic measurements, these studies help researchers in the design of novel compounds with specific properties [4–6,8,11–12] …”

Section: Introductionmentioning

confidence: 99%

Decorating BODIPY with Electron‐Withdrawing NO Group: Spectroelectrochemical Consequences and Computational Investigation

et al. 2021

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4,4‐difluoro‐5,7‐dimethyl‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) and derivatives are an outstanding class of fluorescent dyes. Herein, we report on the introduction of a nitrosyl moiety into the BODIPY structure and its dramatic effect on the observed electrochemical reaction mechanism. 6‐Nitrosyl‐8‐phenyl‐BODIPY and its 5‐nitrosyl positional isomer, compounds 2 and 3, respectively, were obtained from the meso precursor, 8‐phenyl‐BODIPY (1), by nitrosation. Electrochemical studies for 1–3 are reported. Cyclic voltammetry and differential pulse voltammetry in degassed DMF or in MeCN (reduction+oxidation), both with n‐Bu4NPF6 (0.1 mol L−1), were obtained. Compound 1 displays the usual behaviour for 8‐phenyl substituted BODIPYs. The addition of the acceptor nitroso group in compounds 2 (in position β) and 3 (in position α), leads to a different profile. For all the compounds, the nitroso group greatly facilitates the reductions. For compound 3 (EpIc=−0.238 V), the first to be reduced is the nitroso group, due to the stability of the electrogenerated radical anion, along with non‐bonding interactions with the electronegative boron difluoride. This is different from compound 2 (EpIc=−0.351 V) with a β‐nitroso group, where the nitroso‐based facilitated reduction occurs in the substituted BODIPY core. Spectroelectrochemistry coupled with analysis through conceptual density functional theory (CDFT) corroborate the voltammetric results and explain the unexpected reactivity differences.

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Highly Efficient Deep‐Red‐ to Near‐Infrared‐Absorbing and Emissive Benzo/Naphtho[b]furan‐Fused Boron Dipyrromethene (BODIPY)

Qiao

et al. 2018

ChemPhotoChem

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Two aryl-fused BODIPY dyes BF-BDP and NF-BDP were synthesized with benzofuran and naphtho [b]furan fusions on the a,bpositions of the BODIPY skeleton, respectively, resulting in large linear conjugated structures. Both molecules were planar and were characterized as intense deep-red/NIR emitters with emission bands tunable by the solution concentration. Their emission bands were red-shifted to l = 730 and 760 nm in vacuum-deposited films.Fluorophores with photoactivity in the deep-red to NIR region (> 650 nm) are of high interest for several applications, such as chemical sensor, [1] bio-imaging label, [2] and organic photovoltaics. [3][4][5] On one hand, however, their relatively low lying emissive excited states allow more possible non-radiative decay routes, which limit the photoluminescent quantum yields (PLQY) of long-wavelength emission. One the other hand, interaction between photons and electrons that is the principle mechanism in all these applications, high stability and low photo-bleaching effect are required. Thus, continuous research efforts have been put into developing and characterizing new deep-red and NIR fluorophores.4,4-Difluoro-4-borata-3a,4a-diaza-s-indacene, abbreviated as BODIPY, is a popular family of dyes characterized by flexible chemical modifications, tunable absorption/emission band, good photo-stability and high fluorescent efficiency. [6,7] Since the typical photo-active region of a BODIPY chromophore is from 450 to 550 nm, several approaches have been realized to achieve deep-red and NIR absorbing/emitting BODIPYs: (1) introduce "push-pull" strategy by introducing electron donating/withdrawing groups; (2) replace meso-carbon atom by a nitrogen atom to obtain aza-BODIPY; (3) extend the p conjugation system by fusing the dipyrromethene core with aryl moieties. [8] Amongst all these methods, aromatic fusion is a promising strategy for the development of high quality emitters, because the extra rigidity provided by the aromatic fusion structure can enhance the thermal/photo-stability and suppress the non-radiative decay routes via the bond vibration and/or rotation. [9][10][11][12] Several recent examples of BODIPY with aromatic fusion along with either a,b-fusion or b-fusion strategy are illustrated in Scheme 1. [13][14][15][16][17][18] Such fused BODIPYs are generally obtained via complex reaction for aryl-fused pyrrole precursors and/or inter-/intra-molecular ring closure, which usually sacrifices the overall yields of the final BODIPYs.

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Two‐Step Synthetic Route toward Asymmetric and Symmetric Boron Dipyrromethenes: Synthesis, Optical Properties, and Electrochemistry

Cited by 19 publications

References 64 publications

Tuning the photophysical properties of BODIPY dyes through extended aromatic pyrroles

Tuning the photophysical properties of BODIPY dyes through extended aromatic pyrroles

Decorating BODIPY with Electron‐Withdrawing NO Group: Spectroelectrochemical Consequences and Computational Investigation

Highly Efficient Deep‐Red‐ to Near‐Infrared‐Absorbing and Emissive Benzo/Naphtho[b]furan‐Fused Boron Dipyrromethene (BODIPY)

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