Multi-stimuli-responsive poly(NIPA-co-HEMA-co-NVP) with spironaphthoxazine hydrogel for optical data storage application

Yang, Xiaoli; Zhou, Lihua; Liu, Le; Zhao, Xin; Lu, Hao

doi:10.1007/s00396-016-3915-6

Cited by 19 publications

(12 citation statements)

References 41 publications

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“…Spiro-thiazine derivatives act as antimycobacterial activity [6]. Recently, spiro compounds have also drawn much attention due to diverse applications in organic functional materials such as circularly polarized luminescence (CPL) materials [7], a new rhodamine-based chemosensor [8], organic light emitting diodes (OLEDs) [9], a high-performance electrophosphorescent device [10], a fluorescent switch [11], optical data storage [12], and so on.…”

Section: Introductionmentioning

confidence: 99%

Design and Crystal Structures of Two New Compounds Fused with 3,4,5-Trimethoxybenzyl Group and 6,10-Dioxaspiro Group

2018

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Two new compounds, 8-(3,4,5-trimethoxybenzylidene)-6,10-dioxaspiro[4,5]decane-7,9-dione (J1) and 8-(3,4,5-trimethoxybenzyl)-6,10-dioxaspiro[4,5]decane-7,9-dione (J2) have been designed and generated by the reaction of 3,4,5-trimethoxybenzaldehyde with 6,10-dioxaspiro[4,5]decane-7,9-dione in different solvents. The 3,4,5-trimethoxybenzyl group of the two compounds connects with the dioxaspiro group via double bond (J1) and single bond (J2), respectively. The crystal structure determinations show that Compound J1 belongs to the triclinic system, space group P-1 with a = 5.4056(11) Å, b = 11.465(2) Å, c = 13.502(3) Å, α = 92.06(3) • Å, β = 91.35(3) • , γ = 93.50(3) • , C 18 H 20 O 7 , Mr = 348.34, V = 834.4(3) Å 3 , Z = 2, Dc = 1.386 g/cm 3 , F(000) = 368. Compound J2 is also of the triclinic system, space group P-1 with a = 8.8778(18) Å, b = 9.5285(19) Å, c = 11.082(4) Å, α = 89.69(3) • , β = 67.38(3) • , γ = 81.68(3) • , C 18 H 22 O 7 , Mr = 250.36, V = 854.9(3) Å 3 , Z = 2, Dc = 1.361 g/cm 3 , F(000) = 372. Both compounds form three-dimensional network structures via C-H•••O intra-and intermolecular hydrogen bonds.

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Section: Introductionmentioning

confidence: 99%

Design and Crystal Structures of Two New Compounds Fused with 3,4,5-Trimethoxybenzyl Group and 6,10-Dioxaspiro Group

2018

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“…The femtosecond TA studies upon 330 nm excitation reveal almost similar photochromic relaxation dynamics of OX(5) and OX-DPP-OX (7), indicating the retention of photophysical properties of OX in OX-DPP-OX(7) despite the presence of the DPP appendage. Upon ultraviolet excitation the benzo [1,3]oxazine ring opens to generate a zwitterionic isomer in less than 135 ps (60 ps in the case of isolated OX(5)) and, in both instances, the photogenerated species reverts spontaneously back to the original one in 1.5−2 ns. The state of the photochromic moiety within the OX-DPP-OX(7) dyad completely regulates the relaxation dynamics of the fluorescent fragment.…”

Section: Discussionmentioning

confidence: 99%

“…In this regard, a novel design of a photochrome− fluorophore−photochrome dyad incorporating photochromic moieties like benzo [1,3]oxazines (Chart 1), a class of fast thermally reversible photochromic molecules 33−37 that combine two fused heterocyclic rings, indoline and oxazine, 38,39 with an exceptional ability to perform numerous cycles with no signs of photodegradation, 39,40 to the skeleton of a suitable fluorophore allows us to have ultrafast switching materials. UV illumination to benzo [1,3]oxazines, uncolored molecules, leads to the cleavage of the C−O bond and consequent opening of the oxazine ring in ∼60 ps with formation of a zwitterionic isomer incorporating a 3H-indolium cation and a 4-nitrophenolate anion that absorbs strongly centered at 440 nm (Figure 1). In addition to this, it is reported that two enantiomers of the ring-closed form of benzo [1,3]oxazines exchange rapidly (nanosecond regime) and exist in thermal equilibrium between the ring-closed and -opened forms and it is substantiated by a single and broad peak of 1 H NMR at 1.3− 1.6 ppm pertaining to two diastereotopic methyl groups of the indoline ring, adjacent to the chiral C-2 center.…”

Section: Introductionmentioning

confidence: 99%

“…UV illumination to benzo [1,3]oxazines, uncolored molecules, leads to the cleavage of the C−O bond and consequent opening of the oxazine ring in ∼60 ps with formation of a zwitterionic isomer incorporating a 3H-indolium cation and a 4-nitrophenolate anion that absorbs strongly centered at 440 nm (Figure 1). In addition to this, it is reported that two enantiomers of the ring-closed form of benzo [1,3]oxazines exchange rapidly (nanosecond regime) and exist in thermal equilibrium between the ring-closed and -opened forms and it is substantiated by a single and broad peak of 1 H NMR at 1.3− 1.6 ppm pertaining to two diastereotopic methyl groups of the indoline ring, adjacent to the chiral C-2 center. 41 This equilibrium can be reversibly moved toward the opened form by the addition of either acid or base.…”

Section: Introductionmentioning

confidence: 99%

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Ultrafast Fluorescence Photoswitch Incorporating Diketopyrrolopyrrole and Benzo[1,3]oxazine

et al. 2017

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With the objective of developing ultrafast fluorescent switch molecules, we have designed and synthesized fluorescence switch molecules incorporating two oxazine photochromes (OX) at the two end of single diketopyrrolopyrrole (DPP) fluorophore giving the shape of the dyad molecule as OX-DPP-OX. For precise characterization, steady-state photophysical properties, acid–base-induced spectroscopic studies and ultrafast transient absorption spectroscopic studies are performed. In acetonitrile (ACN) solution, the benzo[1,3]oxazine ring of studied oxazine derivatives in OX-DPP-OX opens up and reduces the fluorescence intensity of DPP by 66% upon addition of 50 equiv of trifluoroacetic acid (CF3COOH, TFA) and addition of an equivalent amount of base, tetrabutylammonium hydroxide ((C4H9)4NOH, TBAOH), closes the oxazine ring, reverting the fluorescence intensity of the DPP unit back to its original intensity. Likewise, upon 330 nm laser excitation, the oxazine ring opens up in less than 135 ps in ACN solution, reducing the DPP fluorescence by 90%. Both the processes, acidochromic effect and 330 nm laser excitation, generate a 3H-indolium cation, p-nitrophenolate (protonated) and p-nitrophenolate anion, respectively. The photogenerated isomer lives for 1.5–1.9 ns in room temperature and reverts to its original conformer with first-order kinetics. This photochromic dyad tolerates thousands of switching cycles with no sign of degradation. However, the Gibbs free energy of the cationic fragment of their photogenerated isomer and DPP fluorophore is exergonic (ΔG 0 < −0.8) and ultrafast intramolecular electron transfer occurs very fast (in 16 ps time) from DPP moiety to 3H-indolium cation. As a result, the photoinduced transformation of the photochromic component within this dyad results in the effective quenching of the DPP emission. The fluorescence of this photoswitchable compound is modulated on a nanosecond time scale with excellent fatigue resistance under femtosecond (fwhm ∼100 fs) photoexcitation. Thus, the choice of OX as a photochromic component and DPP as fluorescence component can ultimately lead to the development of valuable ultrafast photoswitchable fluorescent probes for designing ultrafast switching devices. Such valuable mechanistic insights into their excitation dynamics can guide the design of novel members of this family of photochromic compounds with improved photochemical properties.

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“…Cross-linked poly(2-hydroxyethylmethacrylate) (poly[HEMA])-based hydrogels have been extensively studied for use in biomedical applications. − Copolymerization of HEMA with other monomers (vinyl, acrylates, methacrylates, etc.) has produced a wide range of stimuli-responsive hydrogels, including pH-responsive, thermoresponsive, photochromic, and electroconductive hydrogels . Hackelbusch et al showed that grafting of the azide-modified poly(HEMA- co -HPMA) with poly( N -isopropylacrylamide) side chains rendered the polymer thermoresponsive .…”

Section: Introductionmentioning

confidence: 99%

Biotechnical Properties of Poly(HEMA-co-HPMA) Hydrogels Are Governed by Distribution among Water States

Abasi

Podstawczyk

Sherback

et al. 2019

ACS Biomater. Sci. Eng.

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Controlling the biotechnical properties of synthetic hydrogels allows their application in a wide range of biomedical fields. Cross-linker concentration and monomer mole ratio of poly(2-hydroxyethylmethacrylate-co-N-(2-hydroxypropyl) methacrylamide) [poly(HEMA-co-HPMA)]-based hydrogels were used to control the degree of hydration and water distribution within constructs. Cross-linker concentrations corresponding to 0.1, 0.5, 1.0, and 3.0 mol % tetraethylene glycol (TEGDA) with HEMA/HPMA mole ratios of 1:0 and 4:1, and poly(HEMA-co-HPMA) of cross-linker concentration corresponding to 1.0 mol % TEGDA with a HEMA/HPMA ratio of 1:1 were investigated for their degree of hydration, water distribution, and corresponding physiochemical and mechanical properties. Copolymerization of HEMA and HPMA was confirmed by Fourier-transform infrared spectroscopy. Both cross-linker concentration and chemical composition (HEMA/HPMA) systematically changed the water content and free/bound water distribution in the polymer, which resulted in different biochemical and transport properties. The addition of 20% HPMA (poly(HEMA-co-HPMA) (4:1)) increased total hydration (25%) and glass-transition temperature (9%) and decreased elastic modulus (31%) and nonfreezable bound water (33%) of the hydrogel. Increasing cross-linker concentration resulted in a stiffer hydrogel with less total water but larger nonfreezable water content. Evaluation of poly(HEMA-co-HPMA) (1:1) revealed that further increase of HPMA content increased the degree of hydration by 25% and decreased nonfreezable water content and elastic modulus by 33 and 16%, respectively, compared to that of poly(HEMA-co-HPMA) (4:1). The hydrogel correspondingly had a higher void fraction and rougher freeze-fractured surface. The diffusion-related processes depended more on water distribution within the hydrogel. The poly(HEMA) showed the fastest swelling kinetics with a concomitant burst release profile of fluorescein isothiocyanate–dextran (a drug surrogate), while the compositions containing HPMA showed a sustained release pattern. The biotechnical properties are illustrative examples of key properties that are influenced by the water distribution rather than the absolute water content of hydrogels.

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Multi-stimuli-responsive poly(NIPA-co-HEMA-co-NVP) with spironaphthoxazine hydrogel for optical data storage application

Cited by 19 publications

References 41 publications

Design and Crystal Structures of Two New Compounds Fused with 3,4,5-Trimethoxybenzyl Group and 6,10-Dioxaspiro Group

Design and Crystal Structures of Two New Compounds Fused with 3,4,5-Trimethoxybenzyl Group and 6,10-Dioxaspiro Group

Ultrafast Fluorescence Photoswitch Incorporating Diketopyrrolopyrrole and Benzo[1,3]oxazine

Biotechnical Properties of Poly(HEMA-co-HPMA) Hydrogels Are Governed by Distribution among Water States

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