New fluorescent imidazo[1,2- a ]pyridine-BODIPY chromophores: Experimental and theoretical approaches, and cell imaging exploration

Wu, You; Yuan, Wei; Ji, Heyi; Qin, Yaru; Zhang, Jin; Li, Hongkun; Li, Yahong; Wang, Yong; Sun, Yufang; Liu, Wei

doi:10.1016/j.dyepig.2017.03.052

Cited by 25 publications

(6 citation statements)

References 76 publications

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“…Prior to the synthesis of the desired complexes, we focused our attention on the (N,O)-donor compounds. To date only a few crystal structures of analogous 2-(2 0 -hydroxyphenyl)imidazo[1,2-a]pyridines can be found in the literature (Stasyuk, Bultinck et al, 2016;Stasyuk, Cywiń ski & Gryko, 2016;Mutai et al, 2008Mutai et al, , 2016Mutai et al, , 2014An et al, 2016;Salunke et al, 2012;Balijapalli & Iyer, 2015;Wu et al, 2017). Among them, two compounds crystallized by some of us (Stasyuk, Bultinck et al,…”

Section: Resultsmentioning

confidence: 99%

Structural, energetic and spectroscopic studies of new luminescent complexes based on 2-(2′-hydroxyphenyl)imidazo[1,2-a]pyridines and 1,2-phenylenediboronic acid

Kutniewska

Jarzembska

Kamiński

et al. 2018

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Three new blue-luminescent complexes of selected imidazo[1,2-a]pyridine derivatives and 1,2-phenylenediboronic acid have been synthesized and structurally characterized using single-crystal X-ray diffraction. Additionally, the crystal structures of two of the (N,O)-donor compounds have been evaluated for the first time. The crystal packing and molecular motifs observed in the studied crystals have been thoroughly analysed, including computational studies, and are also discussed within the context of analogous systems reported in the literature. It appears that the new compounds form different crystal networks with regard to the asymmetric unit content and packing, although some similarities can be found. In all cases a typical centrosymmetric dimer bound via boronic acid groups is formed, characterized by an interaction energy of about À80 kJ mol À1 , while the 2-(2 0 -hydroxyphenyl)imidazo[1,2-a]pyridine complex and its methoxy derivative form solvate structures, somewhat resembling the previously studied 8-oxyquinolinate analogues. As far as the spectroscopic properties are concerned, the lowest energy excitation observed in the studied complexes is based on the highest occupied molecular orbital-lowest unoccupied molecular orbital transition, and both these molecular orbitals are centred predominantly on the (N,O)-donor species according to the results of time-dependent density functional theory. Thus, the charge transfer observed for the 8-oxyquinolinate equivalents does not occur in these cases. Consequently, the spectroscopic behaviour of the series is very much comparable with that of the parent imidazo[1,2-a]pyridine derivatives, if the excited-state intramolecular proton-transfer process does not take place, as shown by the absorption and emission spectra collected in toluene and acetone solutions. Complexation causes a reduction in the Stokes shift compared with the respective (N,O)-donor molecules. research papers Acta Cryst. (2018). B74, 725-737 Sylwia E. Kutniewska et al. Complexes of C 14 H 12 N 2 O 2 and C 13 H 9 BrN 2 O 727 research papers 728 Sylwia E. Kutniewska et al. Complexes of C 14 H 12 N 2 O 2 and C 13 H 9 BrN 2 O Acta Cryst. (2018). B74, 725-737 Figure 2 Crystal packing of the bromine derivative, c. (a) A view along the [100] direction and (b) a view along the [010] direction. research papers Acta Cryst. (2018). B74, 725-737 Sylwia E. Kutniewska et al. Complexes of C 14 H 12 N 2 O 2 and C 13 H 9 BrN 2 O 735 research papers Acta Cryst. (2018). B74, 725-737 Sylwia E. Kutniewska et al. Complexes of C 14 H 12 N 2 O 2 and C 13 H 9 BrN 2 O 737

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Section: Resultsmentioning

confidence: 99%

Structural, energetic and spectroscopic studies of new luminescent complexes based on 2-(2′-hydroxyphenyl)imidazo[1,2-a]pyridines and 1,2-phenylenediboronic acid

Kutniewska

Jarzembska

Kamiński

et al. 2018

Acta Crystallogr B Struct Sci Cryst Eng Mater

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“…56,57 IP-conjugated BODIPY was used as effective fluorescence compound for cell imaging. 58 In this paper, we report the synthesis of IP-integrated TPA/ TPE-based donor−acceptor fluorophores (Scheme 1) and explored the effect of donor structures on the fluorescence properties and stimuli-responsive fluorescence switching. TPA-IP showed dual-state emission, whereas TPE-IP exhibited typical AIE in the solid state.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The imidazo[1,2- a ]pyridine (IP) unit showed good electron acceptor owing to the sp 2 hybridization of the nitrogen atom and also possess moderate LUMO value for facilitating electron injection. , The IP unit was utilized as an electron-acceptor for constructing various donor–acceptor (D–A) emissive materials for applications such as pharmaceuticals, chemical sensing, bioimaging, and optoelectronics. − Deep-blue fluorescence molecules were reported by attaching IP acceptor with various donor units such as phenanthroimidazole . The coupling IP unit with 2-hydroxy phenyl derivatives produced ESIPT molecules with large Stokes shifted solid-state fluorescence and reversible thermofluorochromism. , IP-conjugated BODIPY was used as effective fluorescence compound for cell imaging …”

Section: Introductionmentioning

confidence: 99%

Multistimuli Fluorescence-Responsive TPA/TPE-Imidazo[1,2-a]pyridine π-Conjugated Donor–Acceptor Derivatives and Effect of Donor Structures

Issac,

Ravi,

Chidambaranathan

et al. 2024

Crystal Growth & Design

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Triphenylamine (TPA) and tetraphenylethylene (TPE) πconjugated imidazo[1,2-a]pyridine (IP) donor−acceptor compounds, TPA-IP and TPE-IP, were synthesized, and the TPA/TPE-dependent stimuliresponsive fluorescence switching in the solid and solution state was investigated. TPA-IP and TPE-IP revealed a twisted molecular conformation and adopted opposite molecular dipole arrangement in the solid state. TPA-IP exhibited dual-state fluorescence [λ max = 441 nm (solid) and 387 nm (hexane), quantum yield (Φ f ) = 1.86% (solid) and 0.089 (compared to quinine sulfate)], whereas TPE-IP showed typical aggregation-induced emission in the solid state (λ max = 445, Φ f = 6.21%). Mechanoresponsive studies of TPE-IP showed self-reversible fluorescence switching upon mechanical grinding and acid exposure. In contrast, TPA-IP exhibited reversible fluorescence switching upon mechanical grinding/heating and acid/base exposure. In solution, TPA-IP exhibited pH-dependent tuneable fluorescence from blue to yellow due to protonation of imidazo-pyridine nitrogen including white light emission at optimized acid concentrations. Computational studies of TPA-IP indicated clear charge transfer from TPA donor to IP acceptor, whereas electron density mostly occupied in the IP in highest occupied molecular orbital and lowest unoccupied molecular orbital of TPE-IP, indicating locally excited state emission. This was further supported by electrochemical cyclic voltammetry that showed a relatively low band gap for TPA-IP compared to TPE-IP. Thus, integrating twisted donor (TPA/ TPE) with the imidazo-pyridine acceptor produced fluorophores with donor-dependent tuneable fluorescence and multistimuliresponsive fluorescence switching.

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“…2,3,10,[13][14][15][16][17] Similarly, N-heteroarenes, e.g., imidazo[1,2-a]pyridine (IP), imidazo [2,1-b]thiazole and indole are privileged scaffolds, [18][19][20] given their pharmaceutical, biological and materials science applications. 18,[20][21][22] These motifs are present in several commercially-available drugs (Figure 1), highlighting the importance of these nuclei. [19][20][21] Therefore, they are considered as structures of interest in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Catalyst- and metal-free C(sp2)-H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature

Neto,

Granja,

Scheide

et al. 2023

Preprint

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In this paper, we report an eco-friendly approach for the C(sp2)-H bond selenylation of imidazopyridines and other (N-heteroarenes as well as simple arenes at ambient temperature. This new protocol consists of the reaction between (N-hetero)-arenes and the diorganyl-diselenides and trichloroisocyanuric acid (TCCA)-ethanol reagent system. In a short reaction time, the desired selenylated products were obtained regioselectively in good yields, with tolerance for a wide range of functional groups

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New fluorescent imidazo[1,2- a ]pyridine-BODIPY chromophores: Experimental and theoretical approaches, and cell imaging exploration

Cited by 25 publications

References 76 publications

Structural, energetic and spectroscopic studies of new luminescent complexes based on 2-(2′-hydroxyphenyl)imidazo[1,2-a]pyridines and 1,2-phenylenediboronic acid

Structural, energetic and spectroscopic studies of new luminescent complexes based on 2-(2′-hydroxyphenyl)imidazo[1,2-a]pyridines and 1,2-phenylenediboronic acid

Multistimuli Fluorescence-Responsive TPA/TPE-Imidazo[1,2-a]pyridine π-Conjugated Donor–Acceptor Derivatives and Effect of Donor Structures

Catalyst- and metal-free C(sp2)-H bond selenylation of (N-hetero)-arenes using diselenides and trichloroisocyanuric acid at room temperature

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