Oxidation of 2-amino-substituted BODIPYs providing pyrazine-fused BODIPY trimers

Yokoi, Hiroki; Wachi, Naruhiko; Hiroto, Satoru; Shinokubo, Hiroshi

doi:10.1039/c3cc48738e

Cited by 46 publications

(13 citation statements)

References 16 publications

(1 reference statement)

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“…Various structural modifications on BODIPY have been summarized to obtain far-red and NIR derivatives, 2 mainly by introducing linear aromatic groups, 4 cyclic aromatic groups, 5 N replacing meso-C 6 and conjugated oligomers. [7][8][9] Recently, several BODIPY conjugated oligomers with fused structures have been synthesized showing intensive NIR absorption/ emission bands due to the expansion of p-conjugation. Wakamiya and Yamaguchi 7 developed a,a-benzene fully fused bisBODIPY A (Fig.…”

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confidence: 99%

Fusion and planarization of bisBODIPY: a new family of photostable near infrared dyes

Jiao

et al. 2015

Chem. Commun.

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We have synthesized a new family of directly-fused bisBODIPY BBP 1 through a key FeCl3-mediated intramolecular oxidative cyclodehydrogenation reaction and its derivatives 2 and 3 from the Knoevenagel reaction. These dyes display effective expansion of π-conjugation over the two BODIPYs due to their locked coplanar conformation, showing intriguing electrochemical and spectroscopic properties, such as intensive absorption/emission bands ranging from 676 to 877 nm and high photostability.

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confidence: 99%

Fusion and planarization of bisBODIPY: a new family of photostable near infrared dyes

Jiao

et al. 2015

Chem. Commun.

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“…[53] This protocol has been applied to 2-amino-BODIPYs 39 to produce BODIPY trimers 40 containing ap yrazineu nit in sufficient yield (Scheme20c). [54] Another example of the oxidative coupling of aromatic amines has been reported by He and co-workers (Scheme 21). [55] They prepared p-extended triphenylenes 42 by oxidation of amino-substituted triphenylene 41.I nt his case, they used molecular oxygen alonea sa no xidantf or this coupling reaction.…”

Section: Intermolecular Cànbond-forming Reactions To Form Phenazinedementioning

confidence: 94%

“…In addition, they reported that this protocol works with 2‐amino‐9,10‐disubstituted anthracene derivatives 37 , providing the corresponding dimers 38 (Scheme b) . This protocol has been applied to 2‐amino‐BODIPYs 39 to produce BODIPY trimers 40 containing a pyrazine unit in sufficient yield (Scheme c) …”

Section: Intermolecular Covalent Bond Formation Through Oxidation Of mentioning

confidence: 99%

Synthesis of π‐Functional Molecules through Oxidation of Aromatic Amines

Hiroto

2019

Chemistry An Asian Journal

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In this review,w ef ocus on the synthesiso fp-conjugated functional molecules by the oxidation of aromatic amines, which is one of the most effective methods fort he constructiono fC ÀC, CÀN, and NÀNb onds between two pconjugated molecular units,a nd consider their characteristics and applications. Polyanilines are the most common products of the oxidation of aromatic amines;h owever,a zobenzenes, phenazines, and 1,1'-binaphthyl-2,2'-diaminesm ay be produced in this manner also, depending on the reaction conditions. Recent advances in the methodology of aniline oxidation have led to the development of high-regioselectivity industrial-scale syntheses of optically or electroactive pfunctional dyes containing nitrogen atoms. In particular,t he regioselective fusion of p-extended aromatic amines can be used to prepare distorted p-conjugated molecules under mild reactionc onditions, allowing the construction of unprecedented curved nitrogen-containing p-conjugated molecules.Scheme1.Aniline oxidations.Scheme2.Reactionpathways for aniline oxidation.[a] Prof.

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“…Therefore, nitration reaction is one of the first choices for further derivatization of aromatic compounds. Recently, large π-conjugated materials with a nitro group and their derivatives have attracted continuing attention from many research areas [2][3][4][5][6][7][8][9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC

et al. 2020

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Hexapyrrolohexaazacoronene (HPHAC) is one of the N-containing polycyclic aromatic hydrocarbons in which six pyrroles are fused circularly around a benzene. Despite the recent development of HPHAC analogues, there is no report on direct introduction of functional groups into the HPHAC skeleton. This work reports the first example of nitration reaction of decaethylHPHAC. The structures of nitrodecaethylHPHAC including neutral and two oxidized species (radical cation and dication), intramolecular charge transfer (ICT) character, and global aromaticity of the dication are discussed.

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Oxidation of 2-amino-substituted BODIPYs providing pyrazine-fused BODIPY trimers

Cited by 46 publications

References 16 publications

Fusion and planarization of bisBODIPY: a new family of photostable near infrared dyes

Fusion and planarization of bisBODIPY: a new family of photostable near infrared dyes

Synthesis of π‐Functional Molecules through Oxidation of Aromatic Amines

Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC

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