A new tetraphenylethene-based Schiff base: two crystalline polymorphs exhibiting totally different photochromic and fluorescence properties

Sun, Hao; Sun, Shanshan; Han, Fang-Fang; Ni, Zhong‐Hai; Zhang, Ran; Li, Ming‐De

doi:10.1039/c9tc01312a

Cited by 51 publications

(22 citation statements)

References 40 publications

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“…Based on their fundamental structure of AB-SA, it is reasonable to assume their reversible phtochromic procedure as shown in Fig. 4b , where an excited-state molecular motion occurs between the cis- Keto and trans- Keto forms 44 , 45 . Undoubtedly, the introduction of the alicyclic structure together with substituent variation could easily regulate their excited-state molecular motion behavior, that can be visualize by the photochromic rate from AB-SA, DAMB-SAB, DAMB-SA, to DAMB-SAN.…”

Section: Resultsmentioning

confidence: 99%

BioAIEgens derived from rosin: how does molecular motion affect their photophysical processes in solid state?

et al. 2021

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The exploration of artificial luminogens with bright emission has been fully developed with the advancement of synthetic chemistry. However, many of them face problems like weakened emission in the aggregated state as well as poor renewability and sustainability. Therefore, the development of renewable and sustainable luminogens with anti-quenching function in the solid state, as well as to unveil the key factors that influence their luminescence behavior become highly significant. Herein, a new class of natural rosin-derived luminogens with aggregation-induced emission property (AIEgens) have been facilely obtained with good biocompatibility and targeted organelle imaging capability as well as photochromic behavior in the solid state. Mechanistic study indicates that the introduction of the alicyclic moiety helps suppress the excited-state molecular motion to enhance the solid-state emission. The current work fundamentally elucidates the role of alicyclic moiety in luminogen design and practically demonstrates a new source to large-scalely obtain biocompatible AIEgens.

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Section: Resultsmentioning

confidence: 99%

BioAIEgens derived from rosin: how does molecular motion affect their photophysical processes in solid state?

et al. 2021

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“…Based on their fundamental structure of AB-SA, it is reasonable to assume their reversible phtochromic procedure as shown in Fig. 4B, where an excited-state molecular motion occurs between the cis-and trans-Keto forms [44][45] . Undoubtedly, the introduction of the alicyclic structure together with substituent variation could easily regulate their excited-state molecular motion behavior that can be visualize by the photochromic rate from AB-SA, DAMB-SAB, DAMB-SA, to DAMB-SAN.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

BioAIEgens Derived from Rosin: How Does Molecular Motion Affect Their Photophysical Processes in Solid State?

Cai¹,

Lin²,

Liu³

et al. 2021

Preprint

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<p>The exploration of artificial luminogens with bright emission has been fully developed with the advancement of synthetic chemistry. However, many of them face problems like weakened emission in the aggregated state as well as poor renewability and sustainability. Therefore, the development of renewable and sustainable luminogens with anti-quenching function in the solid state, as well as to unveil the key factors that influence their luminescence behavior become highly significant. Herein, a new class of natural rosin-derived luminogens with aggregation-induced emission property (AIEgens) have been facilely obtained with good biocompatibility and targeted organelle imaging capability as well as photochromic behavior in the solid state. Mechanistic study indicates that the introduction of the alicyclic moiety helps suppress the excited-state molecular motion to enhance the solid-state emission. The current work fundamentally elucidates the role of alicyclic moiety in luminogen design and practically demonstrates a new source to large-scalely obtain biocompatible AIEgens.</p>

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“…[1][2][3][4][5][6][7] Physicochemical properties of polymorphs can be very different and thus having implications how they interact with their environment. 8,9 Especially in pharmaceutical compounds the occurrence of polymorphism has been recognized as an inevitable process, which needs to be screened in an early stage of the development of new molecules in order to avoid undesirable effects when administering the drugs. 10,11 The number of polymorphs is not limited to two, but can be as high as twelve as was recently reported for 5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile (also named ROY).…”

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confidence: 99%

Packing Polymorphism Affecting the Optoelectronic Properties of a π-Conjugated Organic Compound

Roche

Moreau

Dautel

et al. 2021

Crystal Growth & Design

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Benzothieno[3,benzothiophene (BTBT) derivatives are widely employed as hole transport materials in organic field-effect transistors. The electronic properties of these 2 materials depend critically on the crystal packing, which depends on its turn on the choice of the attached functional group. With symmetrically attached alcohol chains the structure may display different packing modes depending on the number of CH2 groups in the alkyl chain. The dipentanol BTBT derivative has two polymorphs I and II, crystallizing from different solvents, with distinct packing modes and consequently different electronic properties. Whereas the conformational changes are very small between I and II and the hydrogen bonding networks in the structures are identical, the adjacent BTBT cores are differently shifted and oriented with respect to each other. It is shown by Density Functional Theory that polymorph I having unfavorable electronic properties is slightly more stable than polymorph II. This is caused by the much more attractive cross stacking between BTBT cores and C5OH chains in I than in II. The stacking in II originates rather from electrostatic interactions between the BTBT cores. The differences and resemblances with the packing modes of the di-butanol and di-hexanol derivatives are discussed. Both polymorphic forms I and II display negative uniaxial thermal expansion, but in different directions with respect to the packing of the molecules. SynopsisThe present study describes the packing polymorphism of a benzothienobenzothiophene derivative containing symmetric hydroxy aliphatic chains of which one form is semiconducting and the other not. Density Functional Theory and Non-Covalent Interaction calculations are used to discriminate the two forms. They are also structurally compared with very similar compounds having one methylene spacer more or less in the aliphatic chain. IntroductionASSOCIATED CONTENT Supporting Information. Crystal structure data of BTBT-C5OH-I and BTBT-C5OH-II, packing similarities between BTBT-C5OH-I and BTBT-C5OH-II and other structures in the Cambridge Structural Database, photomicrographs of crystals of polymorph I and II, thermal expansion data of BTBT-C5-OH-I, atomic displacement plots for the low-temperature structures of I and II with atom labelling, unusual geometric observations (Mogul analysis), 6-molecules clusters for polymorph I and II used for the promolecular NCI calculations, electron density variation between BTBT-C5-OH isolated subunits (DFT calculations). Crystallographic Information Framework (CIF) files for all structural models reported in this paper have been deposited at the Cambridge Structural Database under the numbers CCDC 2059375, 2060594-2060599. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures" AUTHOR INFORMATION

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A new tetraphenylethene-based Schiff base: two crystalline polymorphs exhibiting totally different photochromic and fluorescence properties

Abstract: Different photoinactivation ways resulting from different crystal packing may account for different photochromic and fluorescence properties of the title polymorphs.

Cited by 51 publications

References 40 publications

BioAIEgens derived from rosin: how does molecular motion affect their photophysical processes in solid state?

BioAIEgens derived from rosin: how does molecular motion affect their photophysical processes in solid state?

BioAIEgens Derived from Rosin: How Does Molecular Motion Affect Their Photophysical Processes in Solid State?

Packing Polymorphism Affecting the Optoelectronic Properties of a π-Conjugated Organic Compound

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