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Sheng-huei Hsiao - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis and properties of novel organosoluble and light-colored poly(ester-amide)s and poly(ester-Imide)s with triptycene moiety
    Journal of Polymer Research, 2018
    Co-Authors: Sheng-huei Hsiao, Yu-chuan Liao
    Abstract:

    Two series of new triptycene-containing poly(ester-amide)s and poly(ester-Imide)s were prepared from 1,4-bis(3-aminobenzoyloxy)triptycene with various aromatic dicarboxylic acids and dianhydrides, respectively. The synthesis of the poly(ester-amide)s was achieved by the phosphorylation polyamidation reaction by means of triphenyl phosphite and pyridine, and the synthesis of the poly(ester-Imide)s included ring-opening polyaddition to give poly(amic acid)s followed by thermal imidization and chemical imidization to polyImides. All the poly(ester-amide)s and most of the poly(ester-Imide)s presented good solubility in many organic solvents and could be solution-cast into transparent and flexible films. These poly(ester-amide)s and poly(ester-Imide)s displayed discernible glass-transition temperatures (Tgs) between 242 and 298 °C in the DSC traces and showed moderate thermal stability with 10 wt% loss temperatures above 464 °C in nitrogen or air. These highly optically transparent polymer films possess an ultraviolet-visible absorption cut-off wavelength (λ0) down to 344 nm. 1,4-Bis(4-aminobenzoyloxy)triptycene was also synthesized and used for polymer synthesis; however, less favorable results were obtained.

  • Synthesis and properties of ortho-linked aromatic poly(ester-amide)s and poly(ester-Imide)s bearing 2,3-bis(benzoyloxy)naphthalene units
    Journal of Polymer Research, 2007
    Co-Authors: Wenjeng Guo, Wen-tsuen Leu, Sheng-huei Hsiao
    Abstract:

    Two new naphthalene-ring-containing bis(ester-amine)s, 2,3-bis(4-aminobenzoyloxy)naphthalene ( p - 2 ) and 2,3-bis(3-aminobenzoyloxy)naphthalene ( m - 2 ), were prepared from the condensation of 2,3-dihydroxynaphthalene with 4-nitrobenzoyl chloride and 3-nitrobenzoyl chloride, respectively, followed by catalytic hydrogenation. The novel aromatic poly(ester-amide)s and poly(ester-Imide)s having 2,3-linked bis(benzoyloxy)naphthalene units have been synthesized from the polycondensation reactions of bis(ester-amine)s ( p - 2 and m - 2 ) or an equimolar mixture of 4,4′-oxydianiline and p - 2 or m - 2 with various aromatic dicarboxylic acids and dianhydrides. The synthesis of the poly(ester-amide)s was achieved by the phosphorylation polyamidation reaction by means of triphenyl phosphate, and the synthesis of the poly(ester-Imide)s included ring-opening polyaddition to give poly(amic acid)s followed by chemical imidization to polyImides. Most of the poly(ester-amide)s were readily soluble in various organic solvents. Six poly(ester-amide)s and two poly(ester-Imide)s derived from less rigid diacids and dianhydrides, respectively, were amorphous and could be solution-cast into transparent and tough films with good mechanical properties. Most of the poly(ester-amide)s displayed discernible glass-transition temperatures ( T _gs) between 192 and 223 °C in the DSC traces. All of the poly(ester-Imide)s, except for one sample, showed clear T _g values between 225 and 265 °C by DSC. These poly(ester-Imide)s showed excellent thermal stability with 10 wt% loss temperatures above 460 °C in nitrogen or air.

  • synthesis and characterization of new aromatic poly amide Imide s derived from 1 4 bis 4 aminophenoxy 2 t butylbenzene and various bis trimellitImide s
    Materials Chemistry and Physics, 2000
    Co-Authors: Chin-ping Yang, Sheng-huei Hsiao, Hueiwen Yang
    Abstract:

    Abstract A series of novel t-butyl group-containing poly(amide–Imide)s III a – m were synthesized by the direct polycondensations of 1,4-bis(4-aminophenoxy)-2-t-butylbenzene (BAP-tBB) with various aromatic bis(trimellitImide)s II a – m in N-methyl-2-pyrrolidone (NMP) using triphenyl phosphite and pyridine as condensing agents. Poly(amide–Imide)s III having inherent viscosities between 0.67 and 1.77 dl g−1 were obtained in quantitative yields. Most of the resulting polymers were readily soluble in polar solvents such as NMP and N,N-dimethylacetamide. All of the soluble poly(amide–Imide)s afforded transparent, flexible, and tough films. The glass transition temperatures of these polymers were in the range of 243–300°C, and the 10% weight loss temperatures were above 490°C in nitrogen. The properties of poly(amide–Imide)s III were compared with those of the corresponding poly(amide–Imide)s III′ prepared from the bis(trimellitImide) of BAP-tBB and various aromatic diamines.

  • Synthesis and Properties of Poly(Amide-Imide-Hydrazide)s and Poly(Amide-Imide-1,3,4-Oxadiazole)s
    High Performance Polymers, 2000
    Co-Authors: Sheng-huei Hsiao, Li-min Chang
    Abstract:

    A series of new wholly aromatic and aromatic-aliphatic poly(amide-Imide-hydrazide)s were prepared by the direct polycondensation from p-aminobenzhydrazide with various Imide ring-containing dicarboxylic acids by means of diphenyl phosphite and pyridine. These polymers had inherent viscosities between 0.60 and 1.17 dl g−1. Most of the poly(amide-Imide-hydrazide)s were readily soluble in polar aprotic solvents such as N-methyl-2-pyrrolidone (NMP) and dimethyl sulfoxide (DMSO) and could be solution cast into light yellow, transparent, flexible, and tough films. These poly(amide-Imide-hydrazide)s had Tg in the range 122–211 °C and could be thermally cyclodehydrated in the solid state to the corresponding poly(amide-Imide-1,3,4-oxadiazole)s approximately in the range 250–400 °C, as evidenced by the differential scanning calorimetry thermograms. The thermally converted oxadiazole copolymers exhibited Tg in the range 120–271 °C and did not show significant weight loss before 380 °C in air or nitrogen. Effects of...

  • Synthesis and characterization of new aromatic poly(amide–Imide)s derived from 1,4-bis(4-aminophenoxy)-2-t-butylbenzene and various bis(trimellitImide)s
    Materials Chemistry and Physics, 2000
    Co-Authors: Chin-ping Yang, Sheng-huei Hsiao, Hueiwen Yang
    Abstract:

    Abstract A series of novel t-butyl group-containing poly(amide–Imide)s III a – m were synthesized by the direct polycondensations of 1,4-bis(4-aminophenoxy)-2-t-butylbenzene (BAP-tBB) with various aromatic bis(trimellitImide)s II a – m in N-methyl-2-pyrrolidone (NMP) using triphenyl phosphite and pyridine as condensing agents. Poly(amide–Imide)s III having inherent viscosities between 0.67 and 1.77 dl g−1 were obtained in quantitative yields. Most of the resulting polymers were readily soluble in polar solvents such as NMP and N,N-dimethylacetamide. All of the soluble poly(amide–Imide)s afforded transparent, flexible, and tough films. The glass transition temperatures of these polymers were in the range of 243–300°C, and the 10% weight loss temperatures were above 490°C in nitrogen. The properties of poly(amide–Imide)s III were compared with those of the corresponding poly(amide–Imide)s III′ prepared from the bis(trimellitImide) of BAP-tBB and various aromatic diamines.

Min Yang - One of the best experts on this subject based on the ideXlab platform.

  • Self-Assembling Nonconjugated Poly(amide-Imide) into Thermoresponsive Nanovesicles with Unexpected Red Fluorescence for Bioimaging.
    Biomacromolecules, 2019
    Co-Authors: Junjie Yan, Runlin Yang, Lizhen Wang, Donghui Pan, Xinyu Wang, Meng-zhen Wang, Min Yang
    Abstract:

    Nonconjugated red fluorescent polymers have been increasingly studied to improve the biocompatibility and penetration depth over conventional fluorescent materials. However, the accessibility of such polymers remains challenging due to the scarcity of nonconjugated fluorophores and lacking relevant mechanism of red-shifted fluorescence. Herein, we discovered that the combination of hydrogen bonding and π-π stacking interactions provides nonconjugated poly(amide-Imide) with a large bathochromic shift (>100 nm) from blue-green fluorescence to red emission. The amphiphilic PEGylated poly(amide-Imide) derived from in situ PEGylation self-assembled into nanovesicles in water, which isolated the aminosuccinImide fluorophore from the solvents and suppressed the hydrogen bonds formation between aminosuccinImide fluorophores and water. Therefore, the fluorescence of PEGylated poly(amide-Imide) in water was soundly retained. Furthermore, the strong hydrogen bonding and hydrophobic interactions with water provided PEGylated poly(amide-Imide) with a reversible thermoresponsiveness and presented a concentration-dependent behavior. Finally, accompanied by the excellent biostability and photostability, PEGylated poly(amide-Imide) exhibited as a good candidate for cell imaging.

  • Self-Assembling Nonconjugated Poly(amide-Imide) into Thermoresponsive Nanovesicles with Unexpected Red Fluorescence for Bioimaging
    2019
    Co-Authors: Junjie Yan, Runlin Yang, Lizhen Wang, Donghui Pan, Xinyu Wang, Meng-zhen Wang, Min Yang
    Abstract:

    Nonconjugated red fluorescent polymers have been increasingly studied to improve the biocompatibility and penetration depth over conventional fluorescent materials. However, the accessibility of such polymers remains challenging due to the scarcity of nonconjugated fluorophores and lacking relevant mechanism of red-shifted fluorescence. Herein, we discovered that the combination of hydrogen bonding and π–π stacking interactions provides nonconjugated poly­(amide-Imide) with a large bathochromic shift (>100 nm) from blue-green fluorescence to red emission. The amphiphilic PEGylated poly­(amide-Imide) derived from in situ PEGylation self-assembled into nanovesicles in water, which isolated the aminosuccinImide fluorophore from the solvents and suppressed the hydrogen bonds formation between aminosuccinImide fluorophores and water. Therefore, the fluorescence of PEGylated poly­(amide-Imide) in water was soundly retained. Furthermore, the strong hydrogen bonding and hydrophobic interactions with water provided PEGylated poly­(amide-Imide) with a reversible thermoresponsiveness and presented a concentration-dependent behavior. Finally, accompanied by the excellent biostability and photostability, PEGylated poly­(amide-Imide) exhibited as a good candidate for cell imaging

  • one pot synthesis of soluble and fluorescent aliphatic hyperbranched poly amide Imide with solvent dependent emission
    Journal of Polymer Science Part A, 2017
    Co-Authors: Rongrong Wang, Runlin Yang, Lizhen Wang, Junjie Yan, Donghui Pan, Xinyu Wang, Min Yang
    Abstract:

    Aliphatic hyperbranched poly(amide-Imide) was facilely prepared by employing a functional thiolactone-maleImide monomer. Highly efficient, selective and quantitative properties of amine-maleImide Michael addition and aminolysis of a thiolactone guaranteed the generation of an ABB' thiol-yne intermediate without side products, followed by consecutive thiol-yne click reaction in one-pot. The hyperbranched structure of the poly(amide-Imide) was confirmed by NMR spectroscopy and triple-detector GPC/SEC analysis. Additionally, due to the presence of aminosuccinImide fluorophores and intrinsic physical property of hyperbranched polymers, this aliphatic hyperbranched poly(amide-Imide) possessed solvent-dependent emission and presented good solubility in various organic solvents. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2053–2060

  • One‐pot synthesis of soluble and fluorescent aliphatic hyperbranched poly(amide‐Imide) with solvent‐dependent emission
    Journal of Polymer Science Part A: Polymer Chemistry, 2017
    Co-Authors: Rongrong Wang, Runlin Yang, Lizhen Wang, Junjie Yan, Donghui Pan, Xinyu Wang, Min Yang
    Abstract:

    Aliphatic hyperbranched poly(amide-Imide) was facilely prepared by employing a functional thiolactone-maleImide monomer. Highly efficient, selective and quantitative properties of amine-maleImide Michael addition and aminolysis of a thiolactone guaranteed the generation of an ABB' thiol-yne intermediate without side products, followed by consecutive thiol-yne click reaction in one-pot. The hyperbranched structure of the poly(amide-Imide) was confirmed by NMR spectroscopy and triple-detector GPC/SEC analysis. Additionally, due to the presence of aminosuccinImide fluorophores and intrinsic physical property of hyperbranched polymers, this aliphatic hyperbranched poly(amide-Imide) possessed solvent-dependent emission and presented good solubility in various organic solvents. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2053–2060

  • thiolactone maleImide a functional monomer to synthesize fluorescent aliphatic poly amide Imide with excellent solubility via in situ pegylation
    Polymer Chemistry, 2016
    Co-Authors: Rongrong Wang, Runlin Yang, Yuping Xu, Lizhen Wang, Min Yang
    Abstract:

    Fluorescent poly(amide-Imide)s are promising materials for use in photonics due to their controllable optical properties and excellent flexibility. Although unconventional fluorescent polymers have been flourishing recently, the fluorescence of aliphatic poly(amide-Imide)s has never been realized until now. Their poor solubility and intolerance to reactive groups during synthesis prohibit access for the modification of poly(amide-Imide)s. Here, we synthesize a functional thiolactone-maleImide monomer via copper(I)-catalyzed azide alkyne cycloaddition and employ a strategy combining aminolysis of thiolactones and amine-maleImide Michael addition for the synthesis of fluorescent aliphatic poly(amide-Imide)s with 2-aminosuccinImide fluorophores. Moreover, in situ generated thiols enable the poly(amide-Imide)s to undergo facile PEGylation via a thiol–methacrylate Michael addition reaction to accomplish excellent solubility in organic solvents and in water.

Yu-chuan Liao - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis and properties of novel organosoluble and light-colored poly(ester-amide)s and poly(ester-Imide)s with triptycene moiety
    Journal of Polymer Research, 2018
    Co-Authors: Sheng-huei Hsiao, Yu-chuan Liao
    Abstract:

    Two series of new triptycene-containing poly(ester-amide)s and poly(ester-Imide)s were prepared from 1,4-bis(3-aminobenzoyloxy)triptycene with various aromatic dicarboxylic acids and dianhydrides, respectively. The synthesis of the poly(ester-amide)s was achieved by the phosphorylation polyamidation reaction by means of triphenyl phosphite and pyridine, and the synthesis of the poly(ester-Imide)s included ring-opening polyaddition to give poly(amic acid)s followed by thermal imidization and chemical imidization to polyImides. All the poly(ester-amide)s and most of the poly(ester-Imide)s presented good solubility in many organic solvents and could be solution-cast into transparent and flexible films. These poly(ester-amide)s and poly(ester-Imide)s displayed discernible glass-transition temperatures (Tgs) between 242 and 298 °C in the DSC traces and showed moderate thermal stability with 10 wt% loss temperatures above 464 °C in nitrogen or air. These highly optically transparent polymer films possess an ultraviolet-visible absorption cut-off wavelength (λ0) down to 344 nm. 1,4-Bis(4-aminobenzoyloxy)triptycene was also synthesized and used for polymer synthesis; however, less favorable results were obtained.

Chin-ping Yang - One of the best experts on this subject based on the ideXlab platform.

  • Fluorinated Aromatic Polyamides and Poly(amide‐Imide)s: Synthesis and Properties
    Macromolecular Chemistry and Physics, 2005
    Co-Authors: Chin-ping Yang
    Abstract:

    A CF 3 -containing diamine, 4,4'-bis(4-amino-2-trifluoromethylphenoxy)biphenyl (I), was synthesized from 4,4'-biphenol and 2-chloro-5-nitrobenzotrifluoride. The Imide-containing diacids (V a-b and VI a-1 ) were prepared by condensation reaction of amino acids, aromatic diamines and trimellitic anhydride. Then, a series of soluble aromatic polyamides (VII a-f ) and poly(amide-Imide)s (VIII a-b and IX a-1 ) were synthesized from diamine I with various aromatic diacids (II a-f ) and the Imide-containing diacids (V a-b and VI a-1 ) via direct polycondensation with triphenyl phosphate and pyridine. Aromatic polyamides and poly(amide-Imide)s had inherent viscosities of 0.60-0.85 dL/g and 0.52-1.44 dL/g, respectively. All synthesized polymers showed excellent solubility in amide-type solvents such as N-methyl-2-pyrrolidinone, N,N-dimethylacetamide (DMAc) and N-dimethylforamide and afford transparent and tough films by DMAc solvent casting. These polymer films had tensile strengths of 87-135 MPa, elongations to break of 8-22%, and initial moduli of 2.0-3.0 GPa. Glass transition temperature of these polymers were in the range of 259-317 °C, and the poly(amide-Imide)s had better thermal stability than aromatic polyamides. In comparison with the isomeric X series, the IX series exhibited less coloring and showed a lower b* (yellowness index) values than the corresponding IX series.

  • Synthesis and properties of organosoluble poly(amide‐Imide)s with propeller‐shaped 1,1,1‐triphenylethane units in the main chain
    Journal of Polymer Science Part A: Polymer Chemistry, 2001
    Co-Authors: Chin-ping Yang, Ruei-shin Chen, Ching-der Chen
    Abstract:

    A dicarboxylic acid {1,1-bis[4-(4-trimellitimidophenoxy)phenyl]-1-phenylethane (II)} bearing two performed Imide rings was prepared from the condensation of 1,1-bis[4-(4-aminophenoxy)phenyl]-1-phenylethane and trimellitic anhydride in a 1/2 molar ratio. A novel family of poly(amide-Imide)s with inherent viscosities of 0.83–1.51 dL/g was prepared by triphenyl phosphite-activated polycondensation from the diImide-diacid II with various aromatic diamines in a medium consisting of N-methyl-2-pyrrolidinone (NMP), pyridine, and calcium chloride. Because the 1,1,1-triphenylethane group of II was unsymmetrical, most of the resulting polymers showed an amorphous nature and were readily soluble in polar solvents such as NMP and N,N-dimethylacetamide. All the soluble poly(amide-Imide)s afforded tough, transparent, and flexible films, which had tensile strengths ranging from 88 to 102 MPa, elongations at break from 6 to 11%, and initial moduli from 2.23 to 2.71 GPa. The synthesized poly(amide-Imide)s possessed glass-transition temperatures from 250 to 287 °C. The poly(amide-Imide)s exhibited excellent thermal stabilities and had 10% weight losses from 501 to 534 °C under a nitrogen atmosphere. A comparative study of some corresponding poly(amide-Imide)s is also presented. © 2001 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 775–787, 2001

  • Synthesis and properties of poly(amide–Imide)s containing a N-methylcarbazole group
    Colloid & Polymer Science, 2000
    Co-Authors: Chin-ping Yang, Ruei-shin Chen, C.-c. Chang
    Abstract:

    A new dicarboxylic acid monomer containing the N-methylcarbazole and Imide structures, 3,6-bis(trimellitimido)-N-methylcarbazole (I), was prepared from the condensation of 3,6-diamino-N-methylcarbazole (c) and trimellitic anhydride. The diamine c was synthesized in three steps starting from the methylation of carbazole, followed by nitration and catalytic hydrazine reduction. A series of N-methylcarbazole-containing poly(amide–Imide)s were synthesized by direct polycondensation from the diImide–diacid I with various aromatic diamines. These poly(amide–Imide)s had inherent viscosities of 0.66–1.47 dl/g and were readily soluble in a variety of organic solvents, including N-methyl-2-pyrrolidone and N,N-dimethylacetamide (DMAc). Transparent, flexible, and tough films of these polymers could be cast from DMAc solutions, and these films exhibited excellent mechanical strength. The glass-transition temperatures of these poly(amide–Imide)s were in the range 317–362 °C. All the poly (amide–Imide) did not degrade noticeably below 480 °C in nitrogen, and the 10% weight loss temperatures and char yields at 800 °C were above 520 °C and 60% in nitrogen, respectively, indicating high thermal stability.

  • synthesis and properties of poly amide Imide s containing a n methylcarbazole group
    Colloid and Polymer Science, 2000
    Co-Authors: Chin-ping Yang, Ruei-shin Chen, C.-c. Chang
    Abstract:

    A new dicarboxylic acid monomer containing the N-methylcarbazole and Imide structures, 3,6-bis(trimellitimido)-N-methylcarbazole (I), was prepared from the condensation of 3,6-diamino-N-methylcarbazole (c) and trimellitic anhydride. The diamine c was synthesized in three steps starting from the methylation of carbazole, followed by nitration and catalytic hydrazine reduction. A series of N-methylcarbazole-containing poly(amide–Imide)s were synthesized by direct polycondensation from the diImide–diacid I with various aromatic diamines. These poly(amide–Imide)s had inherent viscosities of 0.66–1.47 dl/g and were readily soluble in a variety of organic solvents, including N-methyl-2-pyrrolidone and N,N-dimethylacetamide (DMAc). Transparent, flexible, and tough films of these polymers could be cast from DMAc solutions, and these films exhibited excellent mechanical strength. The glass-transition temperatures of these poly(amide–Imide)s were in the range 317–362 °C. All the poly (amide–Imide) did not degrade noticeably below 480 °C in nitrogen, and the 10% weight loss temperatures and char yields at 800 °C were above 520 °C and 60% in nitrogen, respectively, indicating high thermal stability.

  • synthesis and characterization of new aromatic poly amide Imide s derived from 1 4 bis 4 aminophenoxy 2 t butylbenzene and various bis trimellitImide s
    Materials Chemistry and Physics, 2000
    Co-Authors: Chin-ping Yang, Sheng-huei Hsiao, Hueiwen Yang
    Abstract:

    Abstract A series of novel t-butyl group-containing poly(amide–Imide)s III a – m were synthesized by the direct polycondensations of 1,4-bis(4-aminophenoxy)-2-t-butylbenzene (BAP-tBB) with various aromatic bis(trimellitImide)s II a – m in N-methyl-2-pyrrolidone (NMP) using triphenyl phosphite and pyridine as condensing agents. Poly(amide–Imide)s III having inherent viscosities between 0.67 and 1.77 dl g−1 were obtained in quantitative yields. Most of the resulting polymers were readily soluble in polar solvents such as NMP and N,N-dimethylacetamide. All of the soluble poly(amide–Imide)s afforded transparent, flexible, and tough films. The glass transition temperatures of these polymers were in the range of 243–300°C, and the 10% weight loss temperatures were above 490°C in nitrogen. The properties of poly(amide–Imide)s III were compared with those of the corresponding poly(amide–Imide)s III′ prepared from the bis(trimellitImide) of BAP-tBB and various aromatic diamines.

Lizhen Wang - One of the best experts on this subject based on the ideXlab platform.

  • Self-Assembling Nonconjugated Poly(amide-Imide) into Thermoresponsive Nanovesicles with Unexpected Red Fluorescence for Bioimaging.
    Biomacromolecules, 2019
    Co-Authors: Junjie Yan, Runlin Yang, Lizhen Wang, Donghui Pan, Xinyu Wang, Meng-zhen Wang, Min Yang
    Abstract:

    Nonconjugated red fluorescent polymers have been increasingly studied to improve the biocompatibility and penetration depth over conventional fluorescent materials. However, the accessibility of such polymers remains challenging due to the scarcity of nonconjugated fluorophores and lacking relevant mechanism of red-shifted fluorescence. Herein, we discovered that the combination of hydrogen bonding and π-π stacking interactions provides nonconjugated poly(amide-Imide) with a large bathochromic shift (>100 nm) from blue-green fluorescence to red emission. The amphiphilic PEGylated poly(amide-Imide) derived from in situ PEGylation self-assembled into nanovesicles in water, which isolated the aminosuccinImide fluorophore from the solvents and suppressed the hydrogen bonds formation between aminosuccinImide fluorophores and water. Therefore, the fluorescence of PEGylated poly(amide-Imide) in water was soundly retained. Furthermore, the strong hydrogen bonding and hydrophobic interactions with water provided PEGylated poly(amide-Imide) with a reversible thermoresponsiveness and presented a concentration-dependent behavior. Finally, accompanied by the excellent biostability and photostability, PEGylated poly(amide-Imide) exhibited as a good candidate for cell imaging.

  • Self-Assembling Nonconjugated Poly(amide-Imide) into Thermoresponsive Nanovesicles with Unexpected Red Fluorescence for Bioimaging
    2019
    Co-Authors: Junjie Yan, Runlin Yang, Lizhen Wang, Donghui Pan, Xinyu Wang, Meng-zhen Wang, Min Yang
    Abstract:

    Nonconjugated red fluorescent polymers have been increasingly studied to improve the biocompatibility and penetration depth over conventional fluorescent materials. However, the accessibility of such polymers remains challenging due to the scarcity of nonconjugated fluorophores and lacking relevant mechanism of red-shifted fluorescence. Herein, we discovered that the combination of hydrogen bonding and π–π stacking interactions provides nonconjugated poly­(amide-Imide) with a large bathochromic shift (>100 nm) from blue-green fluorescence to red emission. The amphiphilic PEGylated poly­(amide-Imide) derived from in situ PEGylation self-assembled into nanovesicles in water, which isolated the aminosuccinImide fluorophore from the solvents and suppressed the hydrogen bonds formation between aminosuccinImide fluorophores and water. Therefore, the fluorescence of PEGylated poly­(amide-Imide) in water was soundly retained. Furthermore, the strong hydrogen bonding and hydrophobic interactions with water provided PEGylated poly­(amide-Imide) with a reversible thermoresponsiveness and presented a concentration-dependent behavior. Finally, accompanied by the excellent biostability and photostability, PEGylated poly­(amide-Imide) exhibited as a good candidate for cell imaging

  • one pot synthesis of soluble and fluorescent aliphatic hyperbranched poly amide Imide with solvent dependent emission
    Journal of Polymer Science Part A, 2017
    Co-Authors: Rongrong Wang, Runlin Yang, Lizhen Wang, Junjie Yan, Donghui Pan, Xinyu Wang, Min Yang
    Abstract:

    Aliphatic hyperbranched poly(amide-Imide) was facilely prepared by employing a functional thiolactone-maleImide monomer. Highly efficient, selective and quantitative properties of amine-maleImide Michael addition and aminolysis of a thiolactone guaranteed the generation of an ABB' thiol-yne intermediate without side products, followed by consecutive thiol-yne click reaction in one-pot. The hyperbranched structure of the poly(amide-Imide) was confirmed by NMR spectroscopy and triple-detector GPC/SEC analysis. Additionally, due to the presence of aminosuccinImide fluorophores and intrinsic physical property of hyperbranched polymers, this aliphatic hyperbranched poly(amide-Imide) possessed solvent-dependent emission and presented good solubility in various organic solvents. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2053–2060

  • One‐pot synthesis of soluble and fluorescent aliphatic hyperbranched poly(amide‐Imide) with solvent‐dependent emission
    Journal of Polymer Science Part A: Polymer Chemistry, 2017
    Co-Authors: Rongrong Wang, Runlin Yang, Lizhen Wang, Junjie Yan, Donghui Pan, Xinyu Wang, Min Yang
    Abstract:

    Aliphatic hyperbranched poly(amide-Imide) was facilely prepared by employing a functional thiolactone-maleImide monomer. Highly efficient, selective and quantitative properties of amine-maleImide Michael addition and aminolysis of a thiolactone guaranteed the generation of an ABB' thiol-yne intermediate without side products, followed by consecutive thiol-yne click reaction in one-pot. The hyperbranched structure of the poly(amide-Imide) was confirmed by NMR spectroscopy and triple-detector GPC/SEC analysis. Additionally, due to the presence of aminosuccinImide fluorophores and intrinsic physical property of hyperbranched polymers, this aliphatic hyperbranched poly(amide-Imide) possessed solvent-dependent emission and presented good solubility in various organic solvents. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2053–2060

  • thiolactone maleImide a functional monomer to synthesize fluorescent aliphatic poly amide Imide with excellent solubility via in situ pegylation
    Polymer Chemistry, 2016
    Co-Authors: Rongrong Wang, Runlin Yang, Yuping Xu, Lizhen Wang, Min Yang
    Abstract:

    Fluorescent poly(amide-Imide)s are promising materials for use in photonics due to their controllable optical properties and excellent flexibility. Although unconventional fluorescent polymers have been flourishing recently, the fluorescence of aliphatic poly(amide-Imide)s has never been realized until now. Their poor solubility and intolerance to reactive groups during synthesis prohibit access for the modification of poly(amide-Imide)s. Here, we synthesize a functional thiolactone-maleImide monomer via copper(I)-catalyzed azide alkyne cycloaddition and employ a strategy combining aminolysis of thiolactones and amine-maleImide Michael addition for the synthesis of fluorescent aliphatic poly(amide-Imide)s with 2-aminosuccinImide fluorophores. Moreover, in situ generated thiols enable the poly(amide-Imide)s to undergo facile PEGylation via a thiol–methacrylate Michael addition reaction to accomplish excellent solubility in organic solvents and in water.