Mechanofluorochromic Materials Based on Aggregation‐Induced Emission‐Active Boron Ketoiminates: Regulation of the Direction of the Emission Color Changes

Yoshii, Ryousuke; Suenaga, Kazumasa; Tanaka, Kazuo; Chujo, Yoshiki

doi:10.1002/chem.201500033

Cited by 198 publications

(71 citation statements)

References 38 publications

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“…The series of triads composed of two boron ketoiminates and a central bithiophene unit with various functional groups at both ends were synthesized ( Figure 12). 93 As we expected, these triads provided solid-state emission. Interestingly, the emission colors were clearly changed upon grinding the crystalline sample powders to the point the X-ray diffraction peaks disappeared.…”

Section: Progress In the Development Of Advanced Element-block Materisupporting

confidence: 64%

Recent progress in the development of advanced element-block materials

Gon

Tanaka

Chujo

2017

Polym J

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140

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An element-block is defined as a minimum functional unit composed of heteroatoms. The concept of 'element-block material' for designing advanced materials was proposed in 2015. In this review, the recent progress in material designs based on this concept is described. From our research, several element-blocks as representative examples are selected, and their roles in each material are explained. Initially, research on the development of 'designable hybrids' by employing polyhedral oligomeric silsesquioxane (POSS) is illustrated. Multiple functions of hybrids composed of modified POSS and the significant roles of POSS in bio-related polymeric materials for solving critical problems in conventional 19 F MR probes and for realizing new sensing technologies are demonstrated. Next, solid-state luminescent materials containing o-carborane and group 13 element-blocks are discussed. The materials' highly efficient emission in the solid state and their origins are explained. Furthermore, stimuliresponsive luminescent chromism is summarized. The sensing mechanisms and the application of these materials as sensors are presented in this study. In the last part, we mention optically active element-blocks containing chiral P-stereogenic phosphorus. In this review, the characteristics originating from each element-block are explained.

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Section: Progress In the Development Of Advanced Element-block Materisupporting

confidence: 64%

Recent progress in the development of advanced element-block materials

Gon

Tanaka

Chujo

2017

Polym J

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140

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“…49 A variety of boron ketoiminates with diverse substituent groups at both ends were synthesized, and the substituent effects on the optical properties were investigated. Similar to above, boron ketoiminates exhibited AIE properties.…”

Section: Emissive Solid Materials Based On the Aie Propertymentioning

confidence: 99%

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

2015

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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.

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“…This was attributed to intermolecular interactions, such as halogen−halogen bonding, not present in non-halogensubstituted dyes. 44 Though ML materials have potential for practical applications, logical design of these materials remains challenging. 1,2 Prior work in our group has demonstrated that reversible ML properties of BF 2 bdk dyes bearing alkyl chain substituents are highly dependent on the length of the chain, and thus, their properties can be tuned by varying chain length.…”

Section: ■ Introductionmentioning

confidence: 99%

Modulating Mechanochromic Luminescence Quenching of Alkylated Iodo Difluoroboron Dibenzoylmethane Materials

et al. 2016

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Difluoroboron β-diketonate compounds exhibit solid-state luminescence phenomena. Among these are reversible mechanochromic luminescence (ML), aggregation induced emission (AIE), and mechanochromic luminescence quenching (MLQ). These properties can be tuned by alterations to the molecular structure. Dyes with varying halide substituents exhibit tunable ML, MLQ, and solid-state emission with high quantum yields. A series of difluoroboron dibenzoylmethane (BF 2 dbm) dyes with iodide and alkoxyl substituents (BF 2 dbm(I)OR) were synthesized where R = CH 3 (C1), C 5 H 11 (C5), C 6 H 13 (C6), C 12 H 25 (C12), and C 18 H 37 (C18)). The 4-iodo parent compound BF 2 dbm(I) (H) was made for comparison. By keeping the heavy atom static, the dependence of ML properties on alkyl chain length was probed. The hydrogen derivative is only weakly emissive as a solid and exhibited minimal mechanoresponsive behavior. In contrast, alkoxy dyes exhibited tunable ML and MLQ properties depending on the length of the alkyl chain. Longer chain dyes corresponded to smaller singlet triplet energy gaps, greater triplet emission enhancement (77 K), and longer recovery times after smearing under ambient conditions. Shorter chain dyes have a much greater affinity for the ordered emissive state, as confirmed by atomic force microscopy (AFM). Powder X-ray diffraction (XRD) was performed on pristine dye powders as well as drop-cast films to gauge crystallinity in various forms. Single crystal XRD analysis of the H and C5 dyes revealed significant differences in crystal packing and π−π stacked dimers for dyes bearing alkyl chains and dyes without alkyl chains. Unique I−I and F−π close interactions were discovered in the dye crystals. ■ INTRODUCTIONOrganic stimuli-responsive materials have many potential applications as sensors, for memory storage, security inks, OLED development, criminal justice, and even art and design. 1−8 In particular, organoboron materials are a research area of much interest given their tunable optical properties. 9−15 Boron coordination induces striking luminescent properties in β-diketonates. 16 Difluoroboron β-diketonates (BF 2 bdks) frequently display two-photon absorption cross sections, 17,18 high quantum yields, 18−20 large extinction coefficients, 18−20 tunable absorption in the near-UV range, 18,19 intramolecular charge transfer (ICT) character, 20,21 a range of emission colors in the solid-state, 19,22 oxygen-sensitive room temperature phosphorescence in rigid media such as polymers, 23−25 organic vapor sensitivity, 26,27 and reversible mechanochromic luminescence (ML). 22,28−32 ML materials are so named because they undergo a change in emission color in response to mechanical perturbation. 1−5 Types of ML materials include inorganic and organic molecular solids, 33,34 liquid crystals, 35,36 and polymers, 3,37,38 to name a few. In recent years, many groups have made progress in synthesizing, understanding, and applying ML materials. The first ML report from our group, difluoroboron avobenzone (BF 2 AVB), 28 exhibite...

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Mechanofluorochromic Materials Based on Aggregation‐Induced Emission‐Active Boron Ketoiminates: Regulation of the Direction of the Emission Color Changes

Cited by 198 publications

References 38 publications

Recent progress in the development of advanced element-block materials

Recent progress in the development of advanced element-block materials

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

Modulating Mechanochromic Luminescence Quenching of Alkylated Iodo Difluoroboron Dibenzoylmethane Materials

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