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Article ; Online: Insight into Unusual Supramolecular Self-Assemblies of Terthiophenes Directed by Weak Hydrogen Bonding.

Kumar, Shiv / Van Hecke, Kristof / Meyer, Franck

International journal of molecular sciences

2023 Volume 24, Issue 13

Abstract: A supramolecular self-assembly of semiconducting polymers and small molecules plays an important role in charge transportation, performance, and lifetime of an optoelectronic device. Tremendous efforts have been put into the strategies to self-organize ... ...

Abstract	A supramolecular self-assembly of semiconducting polymers and small molecules plays an important role in charge transportation, performance, and lifetime of an optoelectronic device. Tremendous efforts have been put into the strategies to self-organize these materials. In this regard, here, we present the self-organization of terthiophene and its methyl alcohol derivative with 4,4'-bipyridine (44BiPy). An unexpected 2D layered organization of 5,5″-dimethyl-2,2':5',2″-terthiophene (DM3T) and 44BiPy was obtained and analyzed. Single-crystal X-ray diffraction analysis revealed that DM3T and 44BiPy consist of stacked, almost independent, infinite 2D layers while held together by weak hydrogen bonds. In addition to this peculiar supramolecular arrangement of these compounds, the investigation of their photophysical properties showed strong fluorescence quenching of DM3T by 44BiPy in the solid state, suggesting an efficient charge transfer. On the other hand, the methyl alcohol derivative of terthiophene, DM3TMeOH, organized in a closed cyclic motif with 44BiPy via hydrogen bonds.
MeSH term(s)	Hydrogen Bonding ; Methanol ; Thiophenes ; Crystallography, X-Ray
Chemical Substances	alpha-terthienyl (0P77RAU2RR) ; Methanol (Y4S76JWI15) ; Thiophenes
Language	English
Publishing date	2023-07-05
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2019364-6
ISSN	1422-0067 ; 1422-0067 ; 1661-6596
ISSN (online)	1422-0067
ISSN	1422-0067 ; 1661-6596
DOI	10.3390/ijms241311127
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Versatile Palladium-catalyzed intramolecular cyclization to access new luminescent azaphosphaphenalene motifs.

Simoens, Andreas / Kaczmarek, Anna M / Machado, Ian P / Van Hecke, Kristof / Stevens, Christian V

Chemistry (Weinheim an der Bergstrasse, Germany)

2024 Volume 30, Issue 19, Page(s) e202303072

Abstract: Using a straightforward sequence of diphosphonylation and a Pd-catalysed concerted-metalation-deprotonation (CMD), a synthetic strategy towards polyaromatic phosphorus containing heterocycles was developed. Herein, we report the synthesis and ... ...

Abstract	Using a straightforward sequence of diphosphonylation and a Pd-catalysed concerted-metalation-deprotonation (CMD), a synthetic strategy towards polyaromatic phosphorus containing heterocycles was developed. Herein, we report the synthesis and characterization of new azaphosphaphenalenes, using easily accessible palladium catalysts and starting materials. The key tetrahydroquinoline intermediates of the reaction were synthesised via a fast and effective procedure and could be isolated as such, or further reacted towards the target polyaromatic structures. The obtained products showed interesting luminescent properties and their emission, excitation and quantum yields were evaluated.
Language	English
Publishing date	2024-02-19
Publishing country	Germany
Document type	Journal Article
ZDB-ID	1478547-X
ISSN	1521-3765 ; 0947-6539
ISSN (online)	1521-3765
ISSN	0947-6539
DOI	10.1002/chem.202303072
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Single-Crystal-to-Single-Crystal Photosynthesis of Supramolecular Organoboron Polymers with Dynamic Effects.

Bhandary, Subhrajyoti / Beliš, Marek / Shukla, Rahul / Bourda, Laurens / Kaczmarek, Anna M / Van Hecke, Kristof

Journal of the American Chemical Society

2024 Volume 146, Issue 12, Page(s) 8659–8667

Abstract: The solid-state synthesis of single-crystalline organic polymers, having functional properties, remains an attractive and developing research area in polymer chemistry and materials science. However, light-triggered topochemical synthesis of crystalline ... ...

Abstract	The solid-state synthesis of single-crystalline organic polymers, having functional properties, remains an attractive and developing research area in polymer chemistry and materials science. However, light-triggered topochemical synthesis of crystalline polymers comprising an organoboron backbone has not yet been reported. Here, we describe an intriguing example of single-crystal-to-single-crystal (SCSC) rapid photosynthesis (occurs on a seconds-scale) of two structurally different linear organoboron polymers, driven by environmentally sustainable visible/sun light, obtained from the same monomer molecule. A newly designed Lewis acid-base type molecular B ← N organoboron adduct (consisting of an organoboron core and naphthylvinylpyridine ligands) crystallizes in two solid-state forms featuring the same chemical structure but different 3D structural topologies, namely, monomers
Language	English
Publishing date	2024-02-26
Publishing country	United States
Document type	Journal Article
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/jacs.4c00978
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Article ; Online: Dearomative (3 + 2) Cycloaddition of Indoles for the Stereoselective Assembly of Fully Functionalized Cyclopentanoids.

Qatran Al-Khdhairawi, Amjad Ayad / Yuan, Tengrui / Van Hecke, Kristof / Winne, Johan M

Organic letters

2024

Abstract: The gold(I)-catalyzed dearomative cyclopentannulation of various indoles with 2-ethynyl-1,3-dithiolane is reported. The method generates three new stereocenters with excellent control of relative stereochemistry and is tolerant of diverse ... ...

Abstract	The gold(I)-catalyzed dearomative cyclopentannulation of various indoles with 2-ethynyl-1,3-dithiolane is reported. The method generates three new stereocenters with excellent control of relative stereochemistry and is tolerant of diverse functionalization and substitution patterns on the indoles. The obtained cyclopentane-fused indolines allow for interesting subsequent synthetic manipulations, giving rise to fully substituted cyclopentanes with control of the relative stereochemistry of all five stereocenters. The reported reaction illustrates and elucidates a mechanistic dichotomy underlying gold(I)-catalyzed reactions of 2-ethynyl-1,3-dithiolane.
Language	English
Publishing date	2024-05-02
Publishing country	United States
Document type	Journal Article
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/acs.orglett.4c01139
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Article ; Online: Dithioallyl Cations in Stereoselective Dearomative (3 + 2) Cycloadditions of Benzofurans: Mechanism and Synthetic Applications.

Ryckaert, Bram / Hullaert, Jan / Van Hecke, Kristof / Winne, Johan M

The Journal of organic chemistry

2023 Volume 88, Issue 20, Page(s) 14504–14514

Abstract: A stereoselective dearomative cyclopentannulation of benzofurans is reported. A previously reported dearomative (3 + 2) cycloaddition of indoles with 1,4-dithiane-fused allyl cations was found to lack stereoselectivity when more substituted cyclopentene ... ...

Abstract	A stereoselective dearomative cyclopentannulation of benzofurans is reported. A previously reported dearomative (3 + 2) cycloaddition of indoles with 1,4-dithiane-fused allyl cations was found to lack stereoselectivity when more substituted cyclopentene rings are targeted. However, for benzofuran substrates, excellent levels of stereoselectivity were observed for the same allyl cation reagents under very similar reaction conditions. In this full account, we provide a mechanistic rationale and some design principles that govern the stereoselectivity of the intriguing dearomative transformations using dithioallyl cations and demonstrate how the stereoselectivity depends on electronic factors of the starting materials. The stereoselective methodology is also applied in a straightforward dearomative synthesis of the tricyclic sesquiterpenoid natural product aplysin and its analogues, starting from a simple benzofuran.
Language	English
Publishing date	2023-10-09
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.3c01546
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Article ; Online: Ratiometric Thermometers Based on Rhodamine B and Fluorescein Dye-Incorporated (Nano) Cyclodextrin Metal-Organic Frameworks.

Peng, Min / Kaczmarek, Anna M / Van Hecke, Kristof

ACS applied materials & interfaces

2022 Volume 14, Issue 12, Page(s) 14367–14379

Abstract: Macro- and nanosized core, as well as core-shell, γ-cyclodextrin metal-organic frameworks (γ-CD-MOFs) have been designed and used as platforms for the encapsulation of dye molecules to develop the first CD-MOF-based ratiometric optical thermometer ... ...

Abstract	Macro- and nanosized core, as well as core-shell, γ-cyclodextrin metal-organic frameworks (γ-CD-MOFs) have been designed and used as platforms for the encapsulation of dye molecules to develop the first CD-MOF-based ratiometric optical thermometer materials. A novel dye combination was employed for this purpose,
Language	English
Publishing date	2022-03-21
Publishing country	United States
Document type	Journal Article
ISSN	1944-8252
ISSN (online)	1944-8252
DOI	10.1021/acsami.2c01332
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Article: Ratiometric Thermometers Based on Rhodamine B and Fluorescein Dye-Incorporated (Nano) Cyclodextrin Metal–Organic Frameworks

Peng, Min / Kaczmarek, Anna M. / Van Hecke, Kristof

ACS applied materials & interfaces. 2022 Mar. 21, v. 14, no. 12

2022

Abstract: Macro- and nanosized core, as well as core–shell, γ-cyclodextrin metal–organic frameworks (γ-CD-MOFs) have been designed and used as platforms for the encapsulation of dye molecules to develop the first CD-MOF-based ratiometric optical thermometer ... ...

Abstract	Macro- and nanosized core, as well as core–shell, γ-cyclodextrin metal–organic frameworks (γ-CD-MOFs) have been designed and used as platforms for the encapsulation of dye molecules to develop the first CD-MOF-based ratiometric optical thermometer materials. A novel dye combination was employed for this purpose, i.e., the duo rhodamine B (RhB) and fluorescein (FL). RhB is highly temperature-sensitive, whereas FL is less temperature-sensitive, and its luminescence emission peak is used as a reference. Promising results in terms of thermometric properties were obtained for a series of dye-encapsulated γ-CD-MOF materials based on this dye combination, with high relative sensitivities, even up to 5%K–¹, for the dye-encapsulated 75%RhB-25%FL nanosized γ-CD-MOF, among the highest performance values reported so far for luminescent dual thermometers. In our study, we have additionally developed a simple yet effective preparation method for core–shell γ-CD-MOFs, allowing effective manipulation of the γ-CD-MOF shell growth. The proposed method allows incorporation of the FL and RhB dyes in the γ-CD-MOFs in a more controlled manner, enhancing the efficiency of the developed ratiometric (macro) γ-CD-MOF thermometers.
Keywords	encapsulation ; fluorescein ; luminescence ; rhodamines ; thermometers
Language	English
Dates of publication	2022-0321
Size	p. 14367-14379.
Publishing place	American Chemical Society
Document type	Article
ISSN	1944-8252
DOI	10.1021/acsami.2c01332
Database	NAL-Catalogue (AGRICOLA)

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Article: Crystal structures of three

Xu, Xiaowen / Hoogenboom, Richard / Van Hecke, Kristof

Acta crystallographica. Section E, Crystallographic communications

2021 Volume 77, Issue Pt 9, Page(s) 958–964

Abstract: The synthesis and single-crystal X-ray structures of ... ...

Abstract	The synthesis and single-crystal X-ray structures of three
Language	English
Publishing date	2021-08-24
Publishing country	England
Document type	Journal Article
ZDB-ID	2041947-8
ISSN	2056-9890 ; 1600-5368
ISSN	2056-9890 ; 1600-5368
DOI	10.1107/S2056989021008562
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Photomechanical Motions in Organoboron-Based Phosphorescent Molecular Crystals Driven by a Crystal-State [2 + 2] Cycloaddition Reaction.

Bhandary, Subhrajyoti / Beliš, Marek / Kaczmarek, Anna M / Van Hecke, Kristof

Journal of the American Chemical Society

2022 Volume 144, Issue 48, Page(s) 22051–22058

Abstract: Photoluminescent molecular crystals integrated with the ability to transform light energy into macroscopic mechanical motions are a promising choice of materials for both actuating and photonic devices. However, such dynamic photomechanical effects, ... ...

Abstract	Photoluminescent molecular crystals integrated with the ability to transform light energy into macroscopic mechanical motions are a promising choice of materials for both actuating and photonic devices. However, such dynamic photomechanical effects, based on molecular organoboron compounds as well as phosphorescent crystalline materials, are not yet known. Here we present an intriguing example of photomechanical molecular single crystals of a newly synthesized organoboron containing Lewis acid-base molecular adduct (BN1, substituted triphenylboroxine and 1,2-di(4-pyridyl)ethylene) having a capsule shape molecular geometry. The single crystals of BN1 under UV light exhibit controllable rapid bending-shape recovery, delamination, violent splitting-jumping, and expanding features. The detailed structural investigation by single-crystal X-ray diffraction and
MeSH term(s)	Cycloaddition Reaction
Language	English
Publishing date	2022-11-23
Publishing country	United States
Document type	Journal Article
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/jacs.2c09285
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Article ; Online: Dearomative (3 + 2) Cycloadditions of Unprotected Indoles.

Ryckaert, Bram / Hullaert, Jan / Van Hecke, Kristof / Winne, Johan M

Organic letters

2022 Volume 24, Issue 23, Page(s) 4119–4123

Abstract: The (3 + 2) cycloaddition of various indoles with a dithioallyl cation affords dearomatized cyclopentannulated adducts, with complete control of regioselectivity and excellent chemo- and diastereoselectivity. The success of the reaction critically relies ...

Abstract	The (3 + 2) cycloaddition of various indoles with a dithioallyl cation affords dearomatized cyclopentannulated adducts, with complete control of regioselectivity and excellent chemo- and diastereoselectivity. The success of the reaction critically relies on the use of an excess of very strong Brønsted acid, which paradoxically prevents carbocationic side reactions. The reaction tolerates sensitive functionalities such as basic amines or free hydroxyls, and we demonstrate its use in late stage derivatization of highly functionalized, unprotected indoles.
MeSH term(s)	Acids ; Amines ; Cations ; Cycloaddition Reaction ; Indoles ; Stereoisomerism
Chemical Substances	Acids ; Amines ; Cations ; Indoles
Language	English
Publishing date	2022-06-08
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/acs.orglett.2c01214
Database	MEDical Literature Analysis and Retrieval System OnLINE

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