najoNanosystems: Physics, Chemistry, MathematicsНаносистемы: физика, химия, математика2220-80542305-7971Университет ИТМОnajo-1089Research ArticleCHEMISTRY AND MATERIALS SCIENCEХИМИЯ И НАУКА О МАТЕРИАЛАХNew route to poly (2, 6–diimidaazo (4,5-b: 4’,5-e) pyridinelene-1,4 (2,5-dihydroxy)-phenylene) (PIPD) and high modulus fiber on it basisNew route to poly (2, 6–diimidaazo (4,5-b: 4’,5-e) pyridinelene-1,4 (2,5-dihydroxy)-phenylene) (PIPD) and high modulus fiber on it basisLiJunLiJun

Jun Li

State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology

150001; Harbin

Jun Li

State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology

150001; Harbin

HuZhenHuZhen

Zhen Hu

State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology

150001; Harbin

Zhen Hu

State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology

150001; Harbin

SongYuanjunSongYuanjun

Yuanjun Song

State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology

150001; Harbin

Yuanjun Song

State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology

150001; Harbin

HuangYudongHuangYudong

Yudong Huang

State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology

150001; Harbin

Yudong Huang

State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology

150001; Harbin

yudonghuang@163.comZuevV. V.ZuevV. V.

197101; Kronverkskiy pr. 49; 199004; Bolshoi pr. 31; Saint Petersburg

197101; Kronverkskiy pr. 49; 199004; Bolshoi pr. 31; Saint Petersburg

zuev@hq.macro.ruHarbin Institute of TechnologyКитайHarbin Institute of TechnologyChinaITMO University; Institute of Macromolecular Compounds of the Russian Academy of SciencesРоссияITMO University; Institute of Macromolecular Compounds of the Russian Academy of SciencesRussian Federation20141708202556829835Copyright © Li J., Hu Z., Song Y., Huang Y., Zuev V.V., 20252025Li J., Hu Z., Song Y., Huang Y., Zuev V.V.Li J., Hu Z., Song Y., Huang Y., Zuev V.V.This work is licensed under a Creative Commons Attribution 4.0 License.https://nanojournal.ifmo.ru/jour/article/view/1089

   A novel entry toward poly( 2,6-diimidazo(4,5-b: 4’,5’-e)pyridinylene-1,4(2,5-dihydroxy)-phenylene) (PIPD) has been elaborated. A strategy based on a new route to monomers: a sequential nitration of 2,6-diaminopyridine with KNO3/H2SO4 gives 2,6-diamino- 3,5-dinitro pyridine (DNDAP) in moderate yield and its hydrogenation with Raney nickel as catalyst leads to 2,3,5,6-tetraaminopyridine (TAP) in high yield. The second monomer 2,5-dihydroxyterephthalate (DHTA) was synthesized in high yield as product of sulfur-mediated aromatization of dimethyl succinoyl succinate with subsequent base hydrolysis. PIPD was synthesized by step-by-step heating in polyphosphoric acid with molecular weights of 19 – 25 kilodaltons. The macromolecule of PIPD can be seen as lap-join chain form nano-sized rigid fragment. The as-polymerized liquid crystalline PIPD solution was used for fiber spinning. The tensile strength of PIPD fibers were 1.28 – 1.99 GPa and depended on the molecular weight of the polymer used for spinning.

   A novel entry toward poly( 2,6-diimidazo(4,5-b: 4’,5’-e)pyridinylene-1,4(2,5-dihydroxy)-phenylene) (PIPD) has been elaborated. A strategy based on a new route to monomers: a sequential nitration of 2,6-diaminopyridine with KNO3/H2SO4 gives 2,6-diamino- 3,5-dinitro pyridine (DNDAP) in moderate yield and its hydrogenation with Raney nickel as catalyst leads to 2,3,5,6-tetraaminopyridine (TAP) in high yield. The second monomer 2,5-dihydroxyterephthalate (DHTA) was synthesized in high yield as product of sulfur-mediated aromatization of dimethyl succinoyl succinate with subsequent base hydrolysis. PIPD was synthesized by step-by-step heating in polyphosphoric acid with molecular weights of 19 – 25 kilodaltons. The macromolecule of PIPD can be seen as lap-join chain form nano-sized rigid fragment. The as-polymerized liquid crystalline PIPD solution was used for fiber spinning. The tensile strength of PIPD fibers were 1.28 – 1.99 GPa and depended on the molecular weight of the polymer used for spinning.

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The authors declare that there are no conflicts of interest present.