Fluorescent Boron Complexes of 25‐Oxa­smaragdyrins Containing Axial Silyloxy Groups

Emandi, Ganapathi; Chatterjee, Tamal; Ravikanth, Mangalampalli

doi:10.1002/ejic.201500718

Cited by 6 publications

(3 citation statements)

References 43 publications

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“…The B(III) complexes of meso -triaryl 25-oxasmaragdyrin containing axial silyloxy groups 288 – 290 were synthesized in high yields by treating B(OH) 2 –smaragdyrin with different alkyl/aryl chlorosilanes in toluene in the presence of triethylamine at reflux temperature (Scheme ). The X-ray structure of B(III)–smaragdyrin complex 288 containing trimethylsilyloxy groups revealed that the smaragdyrin macrocycle was almost planar and the −OSiMe 3 groups were oriented in the up and down directions with respect to the macrocycle (Figure b).…”

Section: Smaragdyrinsmentioning

confidence: 99%

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Smaragdyrins and Sapphyrins Analogues

et al. 2016

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Porphyrins and expanded porphyrins have attracted the attention of chemists for a long time in view of their diverse applications in catalysis; as anion, cation, and neutral substrate receptors; as ligands to coordinate large metal ions; as nonlinear optical materials, MRI contrasting agents, and sensitizers for photodynamic therapy (PDT); and more recently as models for aromaticity (both Huckel and Mobius). A diverse range of synthetic expanded porphyrins containing up to 96π electrons have been reported, and their properties have been exploited for various applications. The present Review is only confined to 22π electron expanded porphyrins containing five pyrrole/ heterocyclic rings such as sapphyrins and smaragdyrins. Even though these two macrocycles contain 22π electrons and five pyrrole/heterocyclic rings, they are structurally different. In sapphyrins, the five pyrrole/heterocyclic rings are connected through four meso-carbon bridges and one direct pyrrole−pyrrole bond, whereas in smaragdyrins, the five pyrrole/heterocyclic rings are connected through three mesocarbon bridges and two direct pyrrole−pyrrole bonds. The chemistry of sapphyrins has been well-established in recent years due to the availability of easy and efficient synthetic methods. On the other hand, smaragdyrins are not explored significantly because of their unstable nature. However, recently it was shown that smaragdyrins can be stabilized if one of the pyrrole rings is replaced with a furan ring to afford stable oxasmaragdyrin. The availability of oxasmaragdyrin allowed the exploration of smaragdyrin in recent years. Thus, an attempt has been made in this Review to describe the chemistry of both sapphyrins and smaragdyrins in terms of their synthesis, characterization, metal ion coordination, and anion-recognition properties.

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Section: Smaragdyrinsmentioning

confidence: 99%

“…5.5 Å diameter sapphyrin core 31 (Figure 10a). This stabilization in the solid state was apparently made possible by the five N−H••• F hydrogen bonds with a bond distance of 2.7 Å (140). The solution-state analysis was further performed with increasing aliquots of fluoride in the CH 3 OH solution.…”

Section: Halide Ionsmentioning

confidence: 99%

Smaragdyrins and Sapphyrins Analogues

et al. 2016

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“…5,[19][20][21] However, when starting materials of Boron are air-sensitive such as BPh 3 , 22-24 BF 3 (OEt 2 ), [25][26][27][28][29][30] BBr 3 , 31,32 and (Mes) 2 BF (Mes = 2,4,6-Me 3 C 6 H 2 ) 33 the synthesis must be carried out in special conditions due to their high toxicity and reactivity (Scheme 1). For example, it has been reported the synthesis of derived from quinolate, [34][35][36][37][38] smaragdyrins, 39 difluoroboron, 40,41 BODIPYs, [42][43][44] and three-coordinated molecules using Schlenk line, [45][46][47] with reaction time ranging from 2 to 18 hours, and other multi-step synthesis , which takes around 5 days. 48 Chan et al have reported a green synthetic approach of fluorescent organoboron compounds derived from Schiff bases by microwaveassisted synthesis.…”

Section: Synthesis Of Luminescent Organoboron Materialsmentioning

confidence: 99%

Recent advances of synthesis of Boron derivatives and their applications in bioimaging

Muñoz‐Flores

Molina‐Paredes

Lara‐Cerón

et al. 2018

IJAMB

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The increasing interest in the luminescent boron materials is due to their potential application in diverse areas such as solar cells, optoelectronic devices, and biological imaging materials. Continuous search for the compounds with better properties, luminescent organoboron materials have been gaining more importance, especially in the development of new technologies and novel techniques for bioimaging, which is a powerful tool to analyze the cellular organelles with important value into the cell biology and medical research. Synthesis, properties, and applications of luminescent boron compounds and their application in bioimaging are reviewed.

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Dipyrrin Complexes of Borasiloxane Silanols with Adaptive Hydrogen‐Bonded Conformations in the Crystal and in Solution States

2020

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Dipyrrin complexes of boradisiloxane disilanol 1 and borasiloxane silanol 2 were synthesized as a novel family of BODIPY-siloxane molecular hybrids. Compound 1 formed a selfcomplementary dimer through quadruple hydrogen bond in single crystal, while adopting a monomeric form with an intramolecular hydrogen bond in solution. Thus, the hydrogenbonded conformations were adaptive in the crystalline and solution states. Borasiloxane silanol 2 was isolated as a methyl boronate ester, which also displayed conformational adaptation behaviour in the crystal and solution states. The characteristic features of borasiloxane silanols, such as the flexibility of the [a] Dr. M. Morisue,versa. In this study, we prepared and isolated structurally discrete dipyrrin complexes of borasiloxane silanols, in which the dipyrrin ligand and phenyl rings constitute the "organic" segments and borasiloxane silanols as the "inorganic" portions and explored their dynamic conformational behaviour in the crystal and in solution states. 1886 Scheme 1. Synthesis of dipyrrin complexes of borasiloxane.

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Fluorescent Boron Complexes of 25‐Oxasmaragdyrins Containing Axial Silyloxy Groups

Cited by 6 publications

References 43 publications

Smaragdyrins and Sapphyrins Analogues

Smaragdyrins and Sapphyrins Analogues

Recent advances of synthesis of Boron derivatives and their applications in bioimaging

Dipyrrin Complexes of Borasiloxane Silanols with Adaptive Hydrogen‐Bonded Conformations in the Crystal and in Solution States

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Fluorescent Boron Complexes of 25‐Oxa­smaragdyrins Containing Axial Silyloxy Groups

Cited by 6 publications

References 43 publications

Smaragdyrins and Sapphyrins Analogues

Smaragdyrins and Sapphyrins Analogues

Recent advances of synthesis of Boron derivatives and their applications in bioimaging

Dipyrrin Complexes of Borasiloxane Silanols with Adaptive Hydrogen‐Bonded Conformations in the Crystal and in Solution States

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Fluorescent Boron Complexes of 25‐Oxasmaragdyrins Containing Axial Silyloxy Groups