6-Amino-2,2′-bipyridine as a new fluorescent organic compound

Araki, Koji; Mutai, Toshiki; Shigemitsu, Yasuhiro; Yamada, Masaki; Nakajima, Teruyuki; Kuroda, Shigeyasu; Shimao, Ichiro

doi:10.1039/p29960000613

Cited by 46 publications

(36 citation statements)

References 27 publications

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“…6,6'-Diamino bpy (13) and 4,4'-diamino bpy (16) are the dimeric form of fluorescent 2-aminopyridine (5) and non-fluorescent 4-aminopyridine (7), respectively. Compound (13) exhibited an efficient blue fluorescence (364.5 nm, =0.49, [36], directly reflecting the photophysical properties of their monomer units [13] (Table (1)). However, both the absorption and fluorescence bands of 13 appeared in lower energy regions compared to those of 5, suggesting the importance of the inter-ring interaction within the molecule (Fig.…”

Section: -1 Ring Substitutionmentioning

confidence: 95%

“…(3)). It was found that single amino substitution (14) was sufficient to induce an efficient fluorescence (364.5 nm, = 0.46) and, interestingly, asymmetrically substituted 6-amino-6'-chloro bpy (15) had a much larger quantum yield ( = 0.79) even though fluorescence was observed in a region similar to that of 13 and 14 [36]. These compounds also showed notable blue luminescence in the solid state.…”

Section: -1 Ring Substitutionmentioning

confidence: 99%

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Fluorescent Oligopyridines and their Photo-Functionality as Tunable Fluorophores

Mutai¹,

Araki

2007

COC

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Oligopyridines connected through the 2-and 6-positions have long been the subject of continuing interest because of their high ability to interact with metal ions and/or other molecules, and their transition-metal complexes have been intensely studied for decades because of their characteristic photophysical properties. However, relatively few have been known in regard to the photophysical and photo-functional properties of oligopyridine derivatives. From the late 1990s, fluorescent oligopyridines have been of considerable interest as tunable fluorophores by intermolecular interaction, and the design and synthesis of novel oligopyridine derivatives and their application to fluorescent sensors has increasingly been studied. In this article, we will review recent developments of fluorescent oligopyridines and their photo-functionality.

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Section: -1 Ring Substitutionmentioning

confidence: 95%

Section: -1 Ring Substitutionmentioning

confidence: 99%

Fluorescent Oligopyridines and their Photo-Functionality as Tunable Fluorophores

Mutai¹,

Araki

2007

COC

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“…2, it was found that 6,6'-diamino-2,2'-bipyridine (1a) displayed a relatively strong fluorescence (λ max = 404 nm; Φ = 0.45 in ethanol) in the near-UV region. 9 Based on this finding, other amino and/or chloro substituted bpys were synthesized and studied to find that only 6-aminosubstituted derivatives exhibited efficient fluorescence. The fluorescence of 6-amino-6'-chloro-bpy (3a) was the strongest (λ max = 429 nm; Φ = 0.78 in ethanol) among them.…”

Section: Fig 1 the Basic Structures Composing Of Polypyridine Compomentioning

confidence: 99%

The Recent Current of Fluorescent Polypyridine Compounds Having Photofuctionality

Choi¹

2016

Rapid Communication in Photoscience

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Many kinds of fluorescent polypyridine compounds including bpy and dppz derivatives are described in understanding the recent current of fluorescent materials having photofuctionality. Those polypyridine compounds have the photofunctionality such as the fluorescence recognition and/or photo-switching. Furthermore, those compounds are applicated for the construction of long ranged photoinduced electron/energy transfer system. Various fluorescent π-conjugation systems connected by amide or imine bond as well as the simple fluorescent bpy derivatives are introduced in this review paper. INTRODUCTIONFluorescent artificial receptors are attracting considerable interest in various stages in sensory, biochemical, medical, photoelectronic, and other fields.1 These receptors are composed of the host unit (binding site) and the signaling unit (fluorescent site), and communication between the two units is essential for guest specific response. Though various molecular designs have been proposed in order to develop efficient fluorescent receptors, 2 most of those receptors are designed by introducing molecular recognition site(s) into the known fluorophores.Polypyridine compounds are useful molecular units as a binding site. They have multiple interaction sites, and the number of pyridine units is adjustable. 2,2'-Bipyridine (bpy) is most studied among them due to its excellent property as a bidentate ligand and as a hydrogen bond acceptor.3 Moreover, rational receptor design using more than one bpy can reach selective and strong interaction with guests.

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“…[12,13] The luminescent behaviour of [Pt (1) [14] In addition, several Pt II and Pt IV complexes containing alkylperoxo ligands other than methylperoxo have been reported previously, but none of these have been prepared via an O 2 insertion reaction. [15][16][17][18][19][20] The O 2 insertion reaction into the Pt II -Me bond in the complex [(PN)Pt(Me)(OOMe)] is also affected by light and the authors have proposed a radical mechanism for their insertion reaction.…”

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confidence: 99%

Towards Photocatalytic Alkane Oxidation: The Insertion of Dioxygen into a Platinum(II)–Methyl Bond

Taylor

Law²,

Sunley³

et al. 2009

Angew Chem Int Ed

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Keywords: singlet oxygen, platinum, photosensitiser, alkane oxidation 2 The selective catalytic oxidation of methane and higher alkanes remains one of the great challenges in catalysis research. Considerable progress has been made during the last three decades regarding the C-H activation of alkanes, in particular electrophilic activation reactions with late transition metals. [1][2][3][4] Once C-H bond cleavage has occurred at a metal centre, a functionalisation of the metal carbon bond is required, followed by release of the product and regeneration of the catalyst. In the case of oxidation reactions, this functionalisation of metal alkyl complexes should be carried out ideally with environmentally benign oxidants such as O 2 or H 2 O 2 . In a previous study, we reported the oxidation of dimethyl Pt II complexes with H 2 O 2 to generate cis-dihydroxo Pt IV complexes. [5] The unusual cis isomer was obtained by using amino-substituted bipyridine ligands, which stabilise this isomer through hydrogen bonding. When we extended our work to Pt II methyl complexes containing tridentate amino-substituted terpyridine ligands, we discovered a remarkable reactivity of the diamino substituted terpy Pt II methyl complex towards O 2 .The reaction of 6,6'-diaminoterpyridine (1) Figure 1 and the supporting material for further information). [6] This dimer formation is quite common for terpy Pt II complexes and arises from metal-metal and π-π interactions. [7] It is for example also observed in the solid state structure of [Pt ( Pt II complexes. [9][10][11] Excitation of the charge transfer region at 388 nm results in an emission spectrum with maxima at 580 and 654 nm (see Supplementary Information).Noteworthy, the diamino substituted terpyridine ligand itself also shows photoluminescence. [12,13] The luminescent behaviour of [Pt (1) [14] In addition, several Pt II and Pt IV complexes containing alkylperoxo ligands other than methylperoxo have been reported previously, but none of these have been prepared via an O 2 insertion reaction. [15][16][17][18][19][20] The O 2 insertion reaction into the Pt II -Me bond in the complex [(PN)Pt(Me)(OOMe)] is also affected by light and the authors have proposed a radical mechanism for their insertion reaction. [14] Similarly, the insertion of O 2 into a Pt IV -H bond has been reported to involve a radical pathway, [21] and insertions of O 2 into other transition metal methyl bonds such as Co and Fe methyl complexes proceed via methyl radicals. [22,23] In contrast, two reports on the direct insertion of O 2 into Pd II -H bonds have shown that these insertion reactions are not affected by light. [24,25] Mechanistic investigations suggest that these reactions proceed by a Pd I /HO 2 (triplet) radical pair intermediate or via a stepwise pathway initiated by reductive elimination of HX to form an O 2 -reactive Pd 0 intermediate. [26,27] Dioxygen, in its triplet ground state, is rather unreactive because reactions are spinforbidden and require a triplet-singlet surface crossing on the reaction c...

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6-Amino-2,2′-bipyridine as a new fluorescent organic compound

Cited by 46 publications

References 27 publications

Fluorescent Oligopyridines and their Photo-Functionality as Tunable Fluorophores

Fluorescent Oligopyridines and their Photo-Functionality as Tunable Fluorophores

The Recent Current of Fluorescent Polypyridine Compounds Having Photofuctionality

Towards Photocatalytic Alkane Oxidation: The Insertion of Dioxygen into a Platinum(II)–Methyl Bond

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