Rational shaping of liquid crystalline diacylaminophenyl platforms equipped with chelating fragments, fluorescent dyes, and square planar platinum complexes

Ziessel, Raymond; Camerel, Franck; Donnio, Bertrand

doi:10.1002/tcr.20164

Cited by 21 publications

(16 citation statements)

References 72 publications

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“…Since 1980, mesomorphic crown ethers have started to be widely investigated. For crown-ether containing liquid crystals, crown ether can be positioned at the lateral or central position with respect to the mesogen which can be of different shape, such as, rod, disc, polycatenar, tape-shaped, dendrimer or polymer [5][6][7][8]. Moreover, the cavity size of crown ether determines which type of cations for complexation.…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, the cavity size of crown ether determines which type of cations for complexation. The most studied in the context of liquid crystal is the benzo-15-crown-5, whereby sodium cation can perfectly fit into the crown ether's cavit [7]. This is because that the size of benzo-15-crown-5 is 1.7-2.2 Å and the cationic diameter of NaI is 1.94 Å. Laschat and co-workers have, has synthesized ortho-terphenyl units bearing both lateral and central benzo-15-crown-5 liquid crystals with and without metal complexation [9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

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Sodium Ion Complexation Enforced Columnar Mesophase of Dibenzo[a,c]phenazine Bearing Lateral Crown Ether

Ong

Yan

Yeh

et al. 2015

Molecular Crystals and Liquid Crystals

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The dibenzo [a,c]phenazine discogen having "π -polarization" containing a lateral crown ether and four alkoxy-peripheral side chain, DBPZ-C n were synthesized. These metal-free crown ether DBPZ-C n having four dodecylalkoxy side chains were found to be non-mesogenic. The columnar mesophase can be augmented by complexation of the crown ether moiety with sodium ion for DBPZ-C 12 -Na. XRD investigation revealed the formation of rectangular columnar mesophase for DBPZ-C 12 -Na.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Sodium Ion Complexation Enforced Columnar Mesophase of Dibenzo[a,c]phenazine Bearing Lateral Crown Ether

Ong

Yan

Yeh

et al. 2015

Molecular Crystals and Liquid Crystals

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“…Values for the achiral analogous compounds. [20] In the glassy state, below 40 8 8C, only ashoulder starts to grow around 3.08 8 on the edge of the fundamental peak and the third-order reflections (20) gradually disappear ( Supporting Information, Figure S7), in line with as light 2D lattice distortion preserving the Col arrangements in the glassy state.T he mean distance between the chains slightly decreases upon cooling. In the low-angle region three sharp maxima are detected, the reciprocal spacing of which are in the ratio 1: ffiffi ffi 3 p :2, reflecting the formation of a2 Dh exagonal lattice with constant a = 26 at 80 8 8C.…”

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confidence: 95%

“…[13] In the present case, owing to the presence of chiral lateral chains,ahelical twist of the columns can be envisaged to explain the formation of the CD active nanostructure (see below). [20] In the glassy state, below 40 8 8C, only ashoulder starts to grow around 3.08 8 on the edge of the fundamental peak and the third-order reflections (20) gradually disappear (Supporting Information , Figure S7), in line with as light 2D lattice distortion preserving the Col arrangements in the glassy state.T he mean distance between the chains slightly decreases upon cooling. In the isotropic liquid, only ab road halo is observed in the small angle region together with the one in the wide angle region, reflecting the mean distances between the BPM cores and the chains,respectively.…”

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confidence: 95%

Chiral Side Groups Trigger Second Harmonic Generation Activity in 3D Octupolar Bipyrimidine‐Based Organic Liquid Crystals

et al. 2017

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The design of efficient noncentrosymmetric materials remains the ultimate goal in the field of organic secondorder nonlinear optics.Unlike inorganic crystals currently used in second-order nonlinear optical applications,o rganic materials are an attractive alternative owing to their fast electrooptical response and processability,b ut their alignment into noncentrosymmetric film remains challenging. Here,symmetry breaking by judicious functionalization of 3D organic octupoles allows the emergence of multifunctional liquid crystalline chromophores whichc an easily be processed into large, flexible,t hin, and self-oriented films with second harmonic generation responses competitive to the prototypical inorganic KH 2 PO 4 crystals.T he liquid-crystalline nature of these chiral organic films also permits the modulation of the nonlinear optical properties owingtothe sensitivity of the supramolecular organization to temperature,l eading to the development of tunable macroscopic materials.Noncentrosymmetric (NCS) compounds are of current interest in materials chemistry because of their technologically important second-order nonlinear optical properties, with applications such as second harmonic generation (SHG), electro-optical switching,t elecommunications,o ptical computing, laser technologies,a nd bioimaging. [1] Thed evelopment of numerous nonlinear optical (NLO) inorganic crystals, such as BaB 2 O 4 (BBO), [2] LiB 3 O 5 (LBO), [3] KH 2 PO 4 (KDP), [4] KTiOPO 4 (KTP), [5] AgGaS 2 (AGS), [6] and AgGaGeS 4 (AGGS), [7] has led to significant advances in the application of laser devices from UV to IR spectral wavelengths.N CS crystals of organic molecules such as nitroaniline derivatives are efficient for second-order applications as well. [8] However, crystalline materials lack of processability,and growing large high-quality crystals remains challenging.Alternatively,NLO activity can be achieved in polymeric films by using the poling process,i nw hich as trong electric field is applied to align dipolar organic chromophores inside ap olymer matrix near its glass transition temperature (T g ). [9] Unfortunately,a fter cooling, the obtained NLO-active polymeric materials lack long-term stability and reproducibility of the preparation process,while the strong electric fields used during the poling process can lead to degradation. TheLangmuir-Blodgett film deposition technique has also been used to create NCS films using amphiphilic chromophores,but the tedious monolayerby-monolayer deposition method remains amain obstacle. [10] Liquid-crystalline materials open another route for creating functional organic NLO materials.T hey offer numerous advantages,such as their ease of processing into high-quality thin films,t heir self-healing capacity,a nd the possibility of alignment by shear forces,s urface treatment, or electric or magnetic fields. [11] Thef ormation of NCS liquid crystals containing optically active cores is apromising way to achieve efficient organic thin films for SHG.Engineering organic liquid-crystalline mat...

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“…Stable luminescent σ -alkynyl platinum(II) terpy complexes (17) exhibit RT Col h phases, with BF 4 , Cl, and DOS as counter-anion, and a Col r phase with the dicationic ion (17: R = phythol strand); the dodecyloxy homologs are deprived of mesomorphism [75,76]. These complexes show strong gelation abilities.…”

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confidence: 99%

Metal‐Containing Liquid Crystals

Pucci

Donnio

2014

Handbook of Liquid Crystals

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PreambleMetal-containing liquid crystals, commonly referred to as metallomesogens, a term invented by in the first comprehensive review on the subject, are metal complexes endowed with liquid crystalline (LC) properties. It is now well accepted that the first publication on metallomesogens was by Vorländer [2], who described in 1923 the smectogenic behavior of a series of Schiffbase complexes of diaryl mercury(II), despite earlier but sporadic publications on alkanoate magnesium salts by Heintz [3] and other related alkali metal soaps by Vorländer [4]. This field revived research interest half a century later with the concomitant pioneering publications by Malthête and Billard [5] on nematogenic ferrocene derivatives on the one hand and by Giroud and Mueller-Westerhoff on calamitic nickel(II) and platinum(II) dithiolene complexes (N and SmC phases) on the other hand [6].At first, metallomesogens were simply regarded as mere synthetic curiosities, but once the immense benefits of inserting metals into liquid crystals were acknowledged, activity in this field began to grow apace [1]. Metal-coordination of organic ligands indeed offers the possibility of obtaining a wide diversity of structures and functions (due to specific metal-metal, ligand-ligand, and metal-ligand synergies) as it is possible to combine a large range of potential organic ligands with metal ions of various numbers of coordination (NCs from 1 to 12). And indeed, numerous metallomesogens with new geometries (e.g., based on high coordination numbers) and shapes unattainable in organic systems diverging from standard calamitics and discotics, have been synthesized. Simultaneously, the use of multivalent ligands has also been more generalized and has led to intricate polymetallic systems that are expected to generate new functional supramolecular organizations. Evidently, metals are not limited to this purely structural role and, concomitantly to the production of metallomesogens with low transition temperatures and accessible mesophases, a wide range of physical properties (optical, magnetism, electronic, thermo-and solvatochromism, dichroism, conductivity, etc.), which crucially depend on the choice of the metal ion, can be exploited [7]. Incorporation of metals into modifications have led to new and sophisticated molecular structures, showing that the design of new LC materials is not restricted to simple shape anisotropies.The induction of preselected properties from the single molecular level to the supramolecular network in metal-containing materials is expected to expand the traditional range of technological applications of liquid crystals. It is currently possible to design new and better performing complexes whose structures, mostly unapproachable in purely organic LC systems, are able to induce low transition temperatures and modulate optical, electronic, magnetic, and thermal properties. Nowadays, the molecular design of metallomesogens is essentially based on the multimotif approach because of the spontaneous association of single func...

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Rational shaping of liquid crystalline diacylaminophenyl platforms equipped with chelating fragments, fluorescent dyes, and square planar platinum complexes

Cited by 21 publications

References 72 publications

Sodium Ion Complexation Enforced Columnar Mesophase of Dibenzo[a,c]phenazine Bearing Lateral Crown Ether

Sodium Ion Complexation Enforced Columnar Mesophase of Dibenzo[a,c]phenazine Bearing Lateral Crown Ether

Chiral Side Groups Trigger Second Harmonic Generation Activity in 3D Octupolar Bipyrimidine‐Based Organic Liquid Crystals

Metal‐Containing Liquid Crystals

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