Fluorescence-Enhanced Organogels and Mesomorphic Superstructure Based on Hydrazine Derivatives

Abstract

New low-molecular-mass organic gelators (LMOGs) bearing hydrazine linkage and end-capped by phenyl, namely 1,4-bis[(3,4-bisalkoxyphenyl)hydrozide]phenylene (BPH-n, n = 4, 6, 8, 10), were designed and synthesized. These organogelators have shown great ability to gel a variety of organic solvents to form stable organogels with the critical gelation concentration as low as 8.7 x 10(-4) mol L(-1) (0.06 wt %). The formed gel has a high gel-sol transition temperature (T(gel)) at low gelation concentration. Aggregation-induced emission (AIE) has been observed after gelation though conventional chromophore units not incorporated in BPH-n. The fluorescence quantum yields of xerogel are 2 orders higher than that of dilute solution. In addition, the BPH-n (n = 6, 8, 10) exhibited thermotropic hexagonal column (Col(h)) mesophase, which are stable at room temperature as revealed by differential scanning calorimetry (DSC), polarized optical microscopy (POM), and X-ray diffraction (XRD) studies.

Influence of Aggregation on the Structure and Fluorescent Properties of a Tetraphenylethylene Derivative: a Theoretical Study

“…[1] The phenomenon defined as aggregation induced emission (AIE) has been drawing much attention [2] because of its prominent advantage in devices application for the materials working in solid state, thin film or high concentrations olution.S everal possible mechanism of AIE have been put forward through experimental analysisa nd theoretical calculation, including the restriction of intramolecular rotations, [3] J-type aggregate formation, [4] intramolecular planarization, [5] intermolecular interaction, [5b, 6] intramolecular charget ransfer, [7] the restricted access to ac onical intersection, [8] etc. [1] The phenomenon defined as aggregation induced emission (AIE) has been drawing much attention [2] because of its prominent advantage in devices application for the materials working in solid state, thin film or high concentrations olution.S everal possible mechanism of AIE have been put forward through experimental analysisa nd theoretical calculation, including the restriction of intramolecular rotations, [3] J-type aggregate formation, [4] intramolecular planarization, [5] intermolecular interaction, [5b, 6] intramolecular charget ransfer, [7] the restricted access to ac onical intersection, [8] etc.…”

“…An infrequent phenomenon was observed by Ta ng's group in 2001, in which as ilole derivative is barely emissive in the dilute solution but intensively emissive in the solid phase. [1] The phenomenon defined as aggregation induced emission (AIE) has been drawing much attention [2] because of its prominent advantage in devices application for the materials working in solid state, thin film or high concentrations olution.S everal possible mechanism of AIE have been put forward through experimental analysisa nd theoretical calculation, including the restriction of intramolecular rotations, [3] J-type aggregate formation, [4] intramolecular planarization, [5] intermolecular interaction, [5b, 6] intramolecular charget ransfer, [7] the restricted access to ac onical intersection, [8] etc. Crystallization-induced emission enhancement( CIEE) and switchable lumines-cence of polymorphs were discovered on the basis of AIE subsequently,w hich showed huge potentiali nt he fields of sensore lement, data storagea nd encryption technology.…”

Preparation and Characterization of a Novel Aspirin Derivative with Anti-Thrombotic and Gastric Mucosal Protection Properties

“…On the other hand, the absorption peak of the carbonyl (acetyl) group [C = O(CH 3 )] in Ca-ASP also shifted to lower wave number (1753 to 1745 cm −1 ), and the absorption peak of hydroxyl (νOH) shifted to 3238 cm −1 , indicating that a hydrogen bond was formed between the acetyl and hydroxyl groups [21]. Additional FTIR spectra were measured at 100°C and 200°C (data not shown), which indicated the strength and position of peak representing the acetyl group [C = O(CH 3 )] and hydroxyl (νOH) groups were not changed, and therefore the hydrogen bond between the acetyl group and the hydroxyl group was an intramolecular bond [22]. There were two new absorption peaks, one at 1033 cm −1 and the other at 567 cm −1 , which were due to absorption by phosphate group.…”

Synthesis and mesomorphic behaviour of hexacatenar di-hydrazine derivatives

“…[18][19][20][21][22][23] For example, we reported that tetracatenar hydrazide derivatives showed a stable columnar phase and demonstrated that intermolecular hydrogen bonding played an important role in stabilising the columnar phase. [24] In our recent article, [24][25][26] twin-tapered di-hydrazine derivatives FH-Tn (n = 6, 7, 8, 10) were reported to exhibit a hexagonal columnar phase, and the intermolecular hydrogen bonding motif between the dihydrazine groups was confirmed. We also reported other di-hydrazine derivatives such as FH-n (n = 4,6,8,10) and BPH-n (n = 6, 8, 10) exhibiting a hexagonal columnar phase or a rectangular columnar phase.…”