Halogen-Bonded Photoresponsive Materials

Saccone, Marco; Cavallo, Gabriella; Metrangolo, Pierangelo; Resnati, Giuseppe; Priimägi, Arri

doi:10.1007/128_2014_615

Cited by 32 publications

(30 citation statements)

References 71 publications

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“…XB-based supramolecular materials have something to offer on all these fronts as will be illustrated through the examples given in this subsection. The discussion follows a recent book chapter written by us, 1039 which we refer to for a more comprehensive treatment.…”

Section: Functional Systemsmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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The halogen bond occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. In this fairly extensive review, after a brief history of the interaction, we will provide the reader with a snapshot of where the research on the halogen bond is now, and, perhaps, where it is going. The specific advantages brought up by a design based on the use of the halogen bond will be demonstrated in quite different fields spanning from material sciences to biomolecular recognition and drug design.

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Section: Functional Systemsmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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“…XB is known for its highly tunable properties such as directionality, hydrophobicity, strength and length. [19][20][21][22][23] XB can be defined as an attractive interaction between a positive electrostatic region present on a halogen atom and an electron donor such as Lewis base, anion or radical. 24 The formation of halogen bonds results primarily from electrostatic force.…”

Section: Introductionmentioning

confidence: 99%

Halogen‐Bonded BODIPY Frameworks with Tunable Optical Features**

Özcan

Dedeoglu

Chumakov

et al. 2020

Chemistry A European J

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The ability to tune optical features of BODIPY materials is essential for their photo-related application. However, it is challenging to efficiently tune the crystal packing of BODIPY derivatives because of their complex nature. In this study, such control of BODIPY supramolecular assemblies was achieved by designing a BODIPY containing a halogen bond (XB) acceptor (-NO2) and donor (I, Br) to mediate halogen bonding interactions. The mono halogenated 2 and 4 was unable to form XB, whereas 3 and 5 formed isostructural mono-coordinate motif 3, 5-I (1D tubular structure) and symmetric bifurcated motif 5-II (1D zigzag chains structure) via N-O•••I,Br XB interactions. The results show that the dispersion and electrostatic component are the major source of 3, 5-I and 5-II XB formations. The XB interaction between-NO2 and X (I, Br) promote singlet-to-triplet intersystem crossing and triplet-to-singlet reverse intersystem crossing due to delocalization of oxygen electrons partially onto the Br and I. Then this interaction leads to unexpected fluorescence enhancement of 5-II. Finally, the indirect optical band gaps of the 3, 5-I and 5-II were able to be tuned in the range of 1.9-2.50 eV via XB driven crystal packings.

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“…The mechanical motion has been attributed to the isomerization of azobenzenes in the crystalline state (Bushuyev, Corkery et al, 2014;Bushuyev, Tomberg et al, 2014). Our interest in fluorinated azobenzenes started in 2012 when we developed halogen-bonded photoresponsive polymeric and liquid-crystalline materials, demonstrating that halogen bonding is an efficient supramolecular tool for light-induced surface patterning and photoalignment Priimagi, Saccone et al, 2012;Saccone et al, 2015). Subsequently, we developed a small library of halogen-bonded liquid crystals based on fluorinated azobenzenes that undergo a rich variety of photoinduced phase transitions upon light irradiation (Fernandez-Palacio, Poutanen et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Halogen bonding stabilizes acis-azobenzene derivative in the solid state: a crystallographic study

Saccone

Siiskonen

Fernández-Palacio

et al. 2017

Acta Crystallogr Sect B

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Crystals of trans- and cis-isomers of a fluorinated azobenzene derivative have been prepared and characterized by single-crystal X-ray diffraction. The presence of F atoms on the aromatic core of the azobenzene increases the lifetime of the metastable cis-isomer, allowing single crystals of the cis-azobenzene to be grown. Structural analysis on the cis-azobenzene, complemented with density functional theory calculations, highlights the active role of the halogen-bond contact (N...I synthon) in promoting the stabilization of the cis-isomer. The presence of a long aliphatic chain on the azobenzene unit induces a phase segregation that stabilizes the molecular arrangement for both the trans- and cis-isomers. Due to the rarity of cis-azobenzene crystal structures in the literature, our paper makes a step towards understanding the role of non-covalent interactions in driving the packing of metastable azobenzene isomers. This is expected to be important in the future rational design of solid-state, photoresponsive materials based on halogen bonding.

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Halogen-Bonded Photoresponsive Materials

Cited by 32 publications

References 71 publications

The Halogen Bond

The Halogen Bond

Halogen‐Bonded BODIPY Frameworks with Tunable Optical Features**

Halogen bonding stabilizes acis-azobenzene derivative in the solid state: a crystallographic study

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