The first mesogenic derivative of boron difluoride β-diketonate

Turanova, O. A.; Туранов, А. Н.; Lapaev, Dmitry V.; Гнездилов, О. И.; Lobkov, S. V.; Galyametdinov, Yu. G.

doi:10.1134/s1070363206050124

Cited by 19 publications

(10 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For ac loser investigation of the influence of the substituents, the analysis of the partial charges was extended to seven different MIDA boronates carrying methyl ( 14), phenyl( 15), 4ethoxyphenyl( 8( C 2 ))4 -butoxyphenyl (8( C 4 )), 4-hexyloxyphenyl 8( C 6 ),3 ,4-diethoxyphenyl( 8( C 2 ) 2 ), and3 ,4,5-triethoxyphenyl (8( C 2 ) 3 )u nits at the boron atom ( Figure 9). This study revealed that the substituents have an egligible influence on the electronic structure of the MIDA boronate group.…”

Section: Quantumc Hemical Calculationsmentioning

confidence: 99%

“…For example,t ricoordinated boron compoundsa re Lewis acidic, isoelectronicw ith carbeniumions, possess p-electron-acceptor as well as inductive s-electron-donor capacity,u ndergo formation of tetracoordinate borates, and conjugate adjacent p-systems, whereas compounds containing BÀNb onds are isoelectronic with the corresponding CÀCa nalogues and displays trongl uminescence. [1][2][3][4][5][6][7] With regard to thermotropic liquid crystals, most work hasb een devoted to borondifluoride b-diketonates (or b-enaminoketonates), [8][9][10][11][12][13][14] borondipyrromethene (BODIPY) derivatives (1), [15][16][17][18][19][20][21][22][23][24][25][26][27] and boron clusters (2) [28][29][30][31][32][33][34][35] (Figure 1). In diketonate and BODIPY derivatives such as 1 or subphthalocyanines, the boron atom is surrounded by af latm esogenic p-system, which not only contributes to the liquid crystalline self-assembly,b ut also adds favorable absorption and emission characteristics.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Thermotropic MIDA Boronates as a Case Study for the Role of Dipolar Interactions in Liquid Crystalline Self‐Assembly

Wöhrle

Gündemir

Frey

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

A series of MIDA (N-methylimino diacetic acid) boronates carrying 4-alkoxy, 3,4-bisalkoxy, or 3,4,5-trisalkoxyphenyl substituents were synthesized and their mesomorphic properties characterized by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X-ray diffraction (XRD) techniques such as small- and wide-angle X-ray scattering (SAXS and WAXS, respectively). Most derivatives were liquid crystalline. In the case of mono- and bisalkoxy-substituted derivatives, C chains already induced smectic A (SmA) mesophases despite the bulky MIDA head group. With increasing chain length, columnar hexagonal (Col ) phases replaced SmA phases in the disubstituted series. Quantum chemical calculations on a series of MIDA boronates show that the B-N bond is a dative bond with a positive charge on the boron atom and negative charges on the nitrogen and oxygen atoms. In addition, no π-interaction between the aryl moiety and B-N bond was found, thus the mesogenic unit is electronically decoupled from the MIDA head group. These theoretical findings were supported by IR and Raman spectra as well as by asingle crystal structure analysis of 4-ethoxyphenyl MIDA boronate. Calculations of the electrostatic potential of the MIDA boronate reveal a special polarity pattern that can support the formation of a two-dimensional network and is likely to explain the liquid crystalline self-assembly. The absence of any electronic cross-talk between the MIDA head group and B-aryl or B-alkyl substituents allows the efficient tailoring of the mesophase type through variation of the substituents.

show abstract

Section: Quantumc Hemical Calculationsmentioning

confidence: 99%

mentioning

confidence: 99%

Thermotropic MIDA Boronates as a Case Study for the Role of Dipolar Interactions in Liquid Crystalline Self‐Assembly

Wöhrle

Gündemir

Frey

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Therefore, boron diketonates can be expected to work not only as building blocks for constructing nanomaterials but also as luminogens in these nanostructures. Turanova et al 16,17 reported liquid-crystal polymorphism with 2-alkyl-substituted boron diketonates with their luminescence properties. From the investigation of the influence of the ligand structure on the liquid-crystal properties, it was found that the dodecyloxybenzoate-substituted complex exhibited a mesophase.…”

Section: Building Blocks For Constructing Nanostructures and Supramolmentioning

confidence: 99%

Recent progress of optical functional nanomaterials based on organoboron complexes with β-diketonate, ketoiminate and diiminate

2015

View full text Add to dashboard Cite

The synthesis and application of organoboron complexes are a highly relevant topic owng to their unique characteristics. Based on their emissive properties, these complexes have been used to make novel optical materials and devices; boron β-diketonate is a simple and robust organoboron complex. From a series of recent studies, unique and versatile optical properties have been reported. In this review, we introduce the results of primarily recent studies on boron diketonate and related compounds containing polymers and particularly explain their optical properties. Initially, the multi-emission of boron diketonate derivatives and its application to biotechnology are explained. Next, the formation of nanostructures and its emission properties are demonstrated. The modulation of optical properties by mechanical stress is also presented. Finally, recent progress in the development of solid-emissive materials are shown with boron diketonates and their derivatives, which have aggregation-induced emission properties. The versatility of boron diketonates as a building block for the preparation of functional optical materials is the focus of this review.

show abstract

“…Boron-containing organic molecules have been studied for their mesogenic properties along with luminescence properties ( Camerel et al, 2007 ; Maeda et al, 2010 ; Olivier et al, 2010 ; Sánchez et al, 2010 ; Turanova et al, 2010 ; Benstead et al, 2011a , 2011b ; Maeda et al, 2011 ; Olivier et al, 2012 ; Bando et al, 2013 ; Giziroglu et al, 2014 ; Sánchez et al, 2014 ; Fang et al, 2017 ; Feng et al, 2018 ; Xiong et al, 2018 ; Cheng et al, 2019 ; Liu et al, 2019 ). The very first reports were put forward by Turanova et al wherein the boron difluoride-diketonate complex obtained from a non-mesogenic diketonate exhibited liquid crystalline properties along with photoluminescent properties ( Turanova et al, 2006 ). In concurrence with the previous section, this mini-review will focus on the advances made using diketonates and ketoiminates in the past few years ( Figure 2 ).…”

Section: Self-assembly Into Mesogensmentioning

confidence: 99%

Advances in the Supramolecular Chemistry of Tetracoordinate Boron-Containing Organic Molecules into Organogels and Mesogens

2021

View full text Add to dashboard Cite

Boron-containing organic compounds are well accepted as a class of compounds having excellent photophysical properties. In addition to the unique photophysical properties, the ease of synthesis and structural robustness make tetracoordinate boron complexes ideal for a variety of applications. While significant light has been thrown on their luminescence properties, there is no collective attention to their supramolecular chemistry. In this mini review, we discuss the progress made in the supramolecular chemistry of these compounds which includes their utility as building blocks for liquid crystalline materials and gels largely driven by various non-covalent interactions like H-bonding, CH-π interactions, BF-π interactions and Van der Waals forces. The organoboron compounds presented here are prepared from easy-to-synthesize chelating units such as imines, diiminates, ketoiminates and diketonates. Moreover, the presence of heteroatoms such as nitrogen, oxygen and sulfur, and the presence of aromatic rings facilitate non-covalent interactions which not only favor their formation but also helps to stabilize the self-assembled structures.

show abstract

The first mesogenic derivative of boron difluoride β-diketonate

Cited by 19 publications

References 9 publications

Thermotropic MIDA Boronates as a Case Study for the Role of Dipolar Interactions in Liquid Crystalline Self‐Assembly

Thermotropic MIDA Boronates as a Case Study for the Role of Dipolar Interactions in Liquid Crystalline Self‐Assembly

Recent progress of optical functional nanomaterials based on organoboron complexes with β-diketonate, ketoiminate and diiminate

Advances in the Supramolecular Chemistry of Tetracoordinate Boron-Containing Organic Molecules into Organogels and Mesogens

Contact Info

Product

Resources

About