1,8-Naphthyridine-based boron complexes: visible colorimetric probes for highly selective sensing of phosphoric ion

Wu, Gao Fen; Xu, Qiu Lin; Guo, Lin; Zang, Tie Nan; Tan, Rui; Tao, Si Ting; Ji, Jian Fei; Hao, Rui; Zhang, Jun Feng; Zhou, Ying

doi:10.1016/j.tetlet.2015.07.025

Cited by 18 publications

(11 citation statements)

References 18 publications

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“…From this perspective, 1,8‐naphthyridines (napy) are of particular interest due to the diverse coordination patterns (Figure 1a) reported for their TM complexes, [4] and group 1, [5] 2, [6] 13, [7] and 14 [8] main‐group‐element‐centered Lewis acids. A particularly interesting possibility of napy derivatives is the potential application of their complexes with boron in the field of fluorescence, [7b,c,e] two‐photon absorption, [7j] photoluminescence, [7d] and sensing materials [7f,g] . The close proximity of the two N atoms of the napy unit (ca.…”

Section: Introductionmentioning

confidence: 99%

Diphosphino‐Functionalized 1,8‐Naphthyridines: a Multifaceted Ligand Platform for Boranes and Diboranes

Cui

Dietz

Härterich

et al. 2021

Chemistry A European J

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A 1,8‐naphthyridine diphosphine (NDP) reacts with boron‐containing Lewis acids to generate complexes featuring a number of different naphthyridine bonding modes. When exposed to diborane B2Br4, NDP underwent self‐deprotonation to afford [NDP‐B2Br3]Br, an unsymmetrical diborane comprised of four fused rings. The reaction of two equivalents of monoborane BBr3 and NDP in a non‐polar solvent provided the simple phosphine‐borane adduct [NDP(BBr3)2], which then underwent intramolecular halide abstraction to furnish the salt [NDP‐BBr2][BBr4], featuring a different coordination mode from that of [NDP‐B2Br3]Br. Direct deprotonation of NDP by KHMDS or PhCH2K generates mono‐ and dipotassium reagents, respectively. The monopotassium reagent reacts with one or half an equivalent of B2(NMe2)2Cl2 to afford NDP‐based diboranes with three or four amino substituents.

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Section: Introductionmentioning

confidence: 99%

Diphosphino‐Functionalized 1,8‐Naphthyridines: a Multifaceted Ligand Platform for Boranes and Diboranes

Cui

Dietz

Härterich

et al. 2021

Chemistry A European J

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“…The modification methods of N,N-coordinating organoboron dyes are developed well, including nucleophilic substitution, aldol addition, Knoevenagel condensation, ,, 1,3-dipolar cycloaddition, photocatalytic transformations, and transition metal catalytic reactions (such as Suzuki, , Stille, Negishi, , Sonogashira, C–H arylation, C–H alkylation, and oxidative aromatic coupling). Meanwhile, the postfunctionalization of N,O-coordinating organoboron complexes is still scarcely described, mainly represented by nitro group reduction and N -acylation/alkylation, as well as some examples of Pd-catalytic coupling reactions. , Moreover, the most problematic point of the postfunctionalization of such compounds is their poor stability in hard reaction conditions . The development of effective various C–C and C–heteroatom bond formation reactions can open the way to a large library of new practically important N,O-coordinating organoboron fluorophores.…”

Section: Introductionmentioning

confidence: 99%

Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes

et al. 2020

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An effective method for transition-metal-free postfunctionalization of thiazolo[3,2- c ][1,3,5,2]oxadiazaborinine dyes via direct lithiation of the 1,3-thiazole ring was developed. The reaction allows valuable regioselective C–H modification of these N,O-chelated organoboron chromophores incorporating different groups, including C-, Hal-, Si-, S-, Se-, and Sn-substituents. As a result, a library of novel fluorescent 1,3-thiazole-based organoboron complexes has been synthesized and characterized. The influence of the donor/acceptor strength of the substituent E on the photophysical properties has been established. The compound with a bulky lipophilic substituent (SnBu 3 ) exhibits a relatively high solid-state photoluminescence quantum yield of 44%.

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“…Indeed, difluoroboranyl derivatives containing sulfur are rare. − Moreover, the BF 2 derivatives obtained from NH acids as in the present study ( id est. heterocyclic amides) has also been rarely reported. − It is fair to mention that precursors of BODIPY dyes are NH-acids, but BF 2 compounds based on amides are rare.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Photophysical Properties of Novel Donor–Acceptor N-(Pyridin-2-yl)-Substituted Benzo(thio)amides and Their Difluoroboranyl Derivatives

et al. 2016

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The unprecedented N-pyridin-2-yl substituted benzo(thio)amides were prepared and subsequently converted into the cyclic difluoroboranyl (BF2) derivatives. Mass spectrometry, multinuclear NMR, IR, and elemental analysis confirmed the structure of these compounds. UV/vis and fluorescence spectroscopy as well as first-principle calculations were used to study their properties. For the first time, the influence of both the O/S replacement and presence/absence of the BF2 moiety on the photophysical properties of compounds exhibiting charge transfer properties were examined experimentally and theoretically. We show that the sulfur-containing compound has a much smaller emission quantum yield than its oxygen counterpart. The fluorescence quantum yield is much higher upon formation of the difluoroboranyl complex.

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1,8-Naphthyridine-based boron complexes: visible colorimetric probes for highly selective sensing of phosphoric ion

Cited by 18 publications

References 18 publications

Diphosphino‐Functionalized 1,8‐Naphthyridines: a Multifaceted Ligand Platform for Boranes and Diboranes

Diphosphino‐Functionalized 1,8‐Naphthyridines: a Multifaceted Ligand Platform for Boranes and Diboranes

Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes

Synthesis and Photophysical Properties of Novel Donor–Acceptor N-(Pyridin-2-yl)-Substituted Benzo(thio)amides and Their Difluoroboranyl Derivatives

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