Polymorphic and Isomorphic Cocrystals of a <i>N</i>-Salicylidene-3-aminopyridine with Dicarboxylic Acids: Tuning of Solid-State Photo- and Thermochromism

Carletta, Andrea; Buol, Xavier; Leyssens, Tom; Champagne, Benoı̂t; Wouters, Johan

doi:10.1021/acs.jpcc.6b02734

Cited by 56 publications

(94 citation statements)

References 31 publications

(58 reference statements)

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“…Although any non‐bonded interaction can be used to generate co‐crystals ( e. g. π ‐ π stacking, Coulombic interactions, etc), directional interactions – hydrogen and halogen bonds (denoted H‐bonds and X‐bonds, respectively) – allow for a better control over the interactions found in the resulting co‐crystals. Previously, some of us have shown experimentally that co‐crystallization affects the thermo‐ and photochromic behaviors of N‐salicylideneanilines (or anils), depending on the coformer (the secondary compound) . Anils are dynamical compounds, whose color changes when triggered by external stimuli .…”

Section: Introductionmentioning

confidence: 99%

Periodic DFT Study of the Effects of Co‐Crystallization on a N‐Salicylideneaniline Molecular Switch

et al. 2019

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This work aims at better understanding the complex effects of co‐crystallization on a single salicylideneaniline molecular switch, (E)‐2‐methoxy‐6‐(pyridine‐3‐yliminomethyl)phenol (PYV3), which can tautomerize between an enol and a keto form. A combination of periodic boundary conditions DFT and molecular wavefunction calculations has been adopted for examining a selection of PYV3 co‐crystals, presenting hydrogen bonds (H‐bonds) or halogen bonds (X‐bonds), for which X‐ray diffraction data are available. Three aspects are targeted: i) the energy (H‐bond strength, enol to keto relative energy, and geometry relaxation energies), ii) the geometrical structure (PYV3 to co‐crystal and enol to keto geometrical variations), and iii) the electron distribution (PYV3 to co‐crystal and enol to keto Mulliken charge variations). These allow i) explaining the preference for forming H‐bonds with the nitrogen of the pyridine of PYV3 with respect to the oxygens and the importance of the crystal field, ii) distinguishing the peculiar behavior of the SulfonylDiPhenol (SDP) coformer, which stabilizes the keto form of PYV3, iii) describing the relative stabilization of the enol form upon co‐crystallization (with the exception of SDP) and therefore iv) substantiating the co‐crystallization‐induced reduction of thermochromism observed for several PYV3 co‐crystals.

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Section: Introductionmentioning

confidence: 99%

Periodic DFT Study of the Effects of Co‐Crystallization on a N‐Salicylideneaniline Molecular Switch

et al. 2019

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“…The calculated value of Φ (dihedral angle between aromatic rings) is 31.4° in the RT structure and 31.7° at LT. Despite having Φ >30°, compound 1 has been reported to present only thermochromic behaviour …”

Section: Resultsmentioning

confidence: 99%

“…In contrast, near‐planar conformations ( Φ <20°) should promote a close‐packed molecular arrangement that would hinder rotational motion in the crystal, resulting in non‐photochromic behaviour . However, a number of studies has shown the limit of such an empirical rule . The first method adopted to obtain solid photochromic forms is the introduction of bulky substituents, such as tert ‐butyl or trityl groups, that can act as space openers .…”

Section: Introductionmentioning

confidence: 99%

“…This second approach has the advantage of allowing modification of the crystal structure by keeping the same chromophore component. For this purpose, co‐crystallisation and salification are two effective methods to induce photochromic properties in anil‐based systems . We report co‐crystallisation of N ‐salicylideneaniline/‐aminopyridine derivatives with a halogenated co‐former, 1,2,4,5‐tetrafluoro‐3,6‐diiodobenzene ( I2F4 ) .…”

Section: Introductionmentioning

confidence: 99%

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Halogen‐Bond Effects on the Thermo‐ and Photochromic Behaviour of Anil‐Based Molecular Co‐crystals

Carletta

Spinelli

D’Agostino

et al. 2017

Chemistry A European J

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N-Salicilideneanilines are among the most studied thermo- and photochromic systems in the solid state. Although thermochromism is a general property of crystalline N-salicilideneanilines, photochromism is known in a limited number of cases. As a method for the construction of thermo- and photo-responsive molecular architectures, the co-crystallisation of 1,2,4,5-tetrafluoro-3,6-diiodobenzene (I2F4) with three selected imines of o-vanillin, named 1, 2 and 3, obtained through a condensation reaction with 3-aminopyridine, 4-bromoaniline and 4-iodoaniline, respectively, is reported herein. All crystals and co-crystals have been characterised by means of solid-state complementary techniques (X-ray diffraction, solid-state NMR spectroscopy, absorption and emission spectroscopy). The role of halogen bonding and crystal packing in the optical and chromic properties of all solid materials is discussed. All solids exhibit thermochromic behaviour, and three of them (2, 2 ⋅I2F4 and 3 ⋅I2F4) are also photochromic. Imine derivative 3 crystallises in two different polymorphic forms (3 A and 3 B) and a solvate (3 ). The bromo and iodo derivatives, 2 and 3 B, are isomorphous and form isomorphous co-crystals with I2F4, but behave differently when exposed to UV light because only crystalline 2 is photochromic. Interestingly, the replacement of bromine with iodine seems to turn off the photochromism because crystalline 3 A and 3 , and even the 2 3 solid solution, do not manifest photochromic behaviour.

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“…[109,110] Yana nd Fan [65] prepared three cocrystals (donor, cyanostilbene-based isomers,CS1, CS2, CS3;acceptor, 1, 4-bromotetrafluorobenzene carboxylic acid, OFN,a nd 1,4-diiodotetrafluorobenzene) with solvent-responsive luminescence.M oreover,C S2-OFN presents reversible fluorescence on alternating grinding and light illumination. [109,110] Yana nd Fan [65] prepared three cocrystals (donor, cyanostilbene-based isomers,CS1, CS2, CS3;acceptor, 1, 4-bromotetrafluorobenzene carboxylic acid, OFN,a nd 1,4-diiodotetrafluorobenzene) with solvent-responsive luminescence.M oreover,C S2-OFN presents reversible fluorescence on alternating grinding and light illumination.…”

Section: Stimuli-responsive Luminescent Cocrystalsmentioning

confidence: 99%

Organic Cocrystals: Beyond Electrical Conductivities and Field‐Effect Transistors (FETs)

et al. 2019

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Organic cocrystals based on noncovalent intermolecular interactions (weak interactions) have aroused interest owing to their unpredicted and versatile chemicophysical properties and their applications. In this Minireview, we highlight recent research on organic cocrystals on reducing the aggregation‐caused quenching (ACQ) effect, tuning light emission, ferroelectricity and multiferroics, optical waveguides, and stimuli‐responsiveness. We also summarize the progress made in this field including revealing the structure–property relationships and developing unusual properties. Moreover, we provide a discussion on current achievements, limitations and perspectives as well as some directions and inspiration for further investigation on organic cocrystals.

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Polymorphic and Isomorphic Cocrystals of a N-Salicylidene-3-aminopyridine with Dicarboxylic Acids: Tuning of Solid-State Photo- and Thermochromism

Cited by 56 publications

References 31 publications

Periodic DFT Study of the Effects of Co‐Crystallization on a N‐Salicylideneaniline Molecular Switch

Periodic DFT Study of the Effects of Co‐Crystallization on a N‐Salicylideneaniline Molecular Switch

Halogen‐Bond Effects on the Thermo‐ and Photochromic Behaviour of Anil‐Based Molecular Co‐crystals

Organic Cocrystals: Beyond Electrical Conductivities and Field‐Effect Transistors (FETs)

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