Asymmetric core-expanded aza-BODIPY analogues: facile synthesis and optical properties

Liu, Hui; Lü, Hua; Zhou, Zhikuan; Shimizu, Soji; Li, Zhifang; Kobayashi, Nagao; Shen, Zhen

doi:10.1039/c4cc06704e

Cited by 74 publications

(37 citation statements)

References 24 publications

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“…[6][7][8][9][10][11] It seems that low-symmetrization of the structures is quite effective to cause more energetically distinguished ground and excited states to enlarge the Stokes shi. 12 However, the synthesis of BOPIM dyes is tedious because of the low synthetic yields. On the other hand, the chemical stability of BOPIM dyes needs to be enhanced because they tend to decompose under basic conditions.…”

Section: Introductionmentioning

confidence: 99%

Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence

et al. 2019

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Section: Introductionmentioning

confidence: 99%

Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence

et al. 2019

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“…Indeed, the crystal packing of 2 a was confirmed to have a J‐type arrangement, with an interplanar distance of 3.67 Å and a zigzag pattern (Figure a). This type of packing in conjunction with a large Stokes shift tends to minimize self‐absorption (self‐quenching),– which leads to the relatively strong fluorescence of 2 a in the solid state. In contrast, the fluorescence maxima of 3 and 4 were not shifted, which indicated that J‐type interactions were not dominant for these compounds.…”

Section: Resultsmentioning

confidence: 99%

Color‐Tunable Solid‐State Fluorescence Emission from Carbazole‐Based BODIPYs

Maeda

Todaka

Ueda

et al. 2016

Chemistry A European J

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Several carbazole-based boron dipyrromethene (BODIPY) dyes were synthesized by organometallic approaches. Thiazole, benzothiazole, imidazole, benzimidazole, triazole, and indolone substituents were introduced at the 1-position of the carbazole moiety, and boron complexation of each dipyrrin generated the corresponding compounds 1, 2 a, and 3-6. The properties of these products were investigated by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, X-ray crystallography, and DFT calculations. These compounds exhibited large Stokes shifts, and compounds 1, 2 a, and 3-5 fluoresced both in solution and in the solid state. Complex 2 a showed the highest fluorescence quantum yield (ΦF ) in the solid state, therefore boron complexes of the carbazole-benzothiazole hybrids 2 b-f, which had several different substituents, were prepared and the effects of the substituents on the photophysical properties of the compounds were examined. The fluorescence properties showed good correlation with the results of crystal-packing analyses, and the dyes exhibited color-tunable solid-state fluorescence.

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“…To generate large Stokes shifts and restrict the planarity of the parent benchmark compounds, many modifications have been introduced, such as the inclusion of special moieties at the (aza)BODIPY core, including bulky groups and tetraphenylethene units, the formation of J ‐aggregates with a meso ‐CF 3 group or spiro‐structures with diaryl or dicarboxylate chelates, asymmetrization of the (aza)BODIPY core, development of new types of asymmetrical BF 2 complexes, such as the replacement of a pyrrole by a pyridine ring, and alteration of ligand through contraction or expansion of its core (Figure ).…”

Section: Introductionmentioning

confidence: 99%

A Simple Central Seven‐Membered BOPYIN: Synthesis, Structural, Spectroscopic Properties, and Cellular Imaging Application

Zhang

Yan

et al. 2019

Chemistry A European J

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A two‐step, one‐flask synthesis of central seven‐membered borondifluoride‐3,3‐dimethyl‐2‐[2‐(2‐pyrrolyl)ethenyl] indole (BOPYIN) ligands has been developed by using the unexplored 3,3‐dimethyl‐2‐[2‐(2‐pyrrolyl)ethenyl] indole. The simple synthetic approach has enabled modification of the electronic structure by changing the substituents on the indole unit. X‐ray analysis indicated that conformations of the seven‐membered BF2 complex including BOPYIN and diazaborepin differ from that of the five‐ and six‐membered organoboron complexes. Interestingly, the bond angle of the N⋅⋅⋅B−N bond increases with the number of atoms in the core ring, based on Baeyer strain theory. These unsymmetric BOPYIN derivatives have excellent photophysical properties, including high fluorescence quantum yields, except for BOPYIN‐4 in the solution state, large Stokes shifts, and good molar absorptivity. The dipole moment of BOPYIN‐3 in the first excited singlet state and ground state was demonstrated by a linear Lippert–Mataga plot. The absorption and emission spectra were not mirror images for BOPYIN‐1–3 and 5, in contradiction to Kasha's rule, as determined by TDDFT. The synthesized BOPYINs have been shown to be biocompatible fluorophores in cell bioimaging.

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Asymmetric core-expanded aza-BODIPY analogues: facile synthesis and optical properties

Abstract: Significantly large Stokes shifts and enhanced solid state emissions were achieved in a novel series of asymmetric core-expanded aza-BODIPY analogues, 4a-4d, synthesized by a facile and scalable two-step reaction in high yields.

Cited by 74 publications

References 24 publications

Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence

Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence

Color‐Tunable Solid‐State Fluorescence Emission from Carbazole‐Based BODIPYs

A Simple Central Seven‐Membered BOPYIN: Synthesis, Structural, Spectroscopic Properties, and Cellular Imaging Application

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