Skip to content
DraconiticResearch
Search Sources API
203,948 studies31 sourcesUpdated 17 min ago
Peer-reviewedCC BY 4.0Polymers

Synthesis and Properties of Semi-Alicyclic Polyimides Based on an Asymmetric Diamine from Renewable Menthofuran

  • Lei Xiong1
  • Xuwen Sun1
  • Tao Yuan1
  • Bing Xiong2
  • Yanxiang Mao3
  • Haixia Qi3
  • Feng Liu3
  1. 1School of Pharmacy, Nanchang Medical College, Nanchang 330052, China
  2. 2College of Science and Technology, Nanchang University, Gongqingcheng 332020, China
  3. 3School of Chemistry and Chemical Engineering, Nanchang University, Nanchang 330031, China
Open at sourceDOICite

Abstract

Conventional aromatic polyimides suffer from poor solubility, high water absorption and low visible-light transmittance due to strong interchain charge transfer complex (CTC) interactions, limiting their microelectronic and optoelectronic applications. Here, a novel asymmetric bio-based diamine ENDAP bearing a 3,4,5,6,7,8-hexahydro-2H-2,4a-epoxynaphthalene-3,4-diyl (HEN) alicyclic skeleton was synthesized from menthofuran via a four-step route. ENDAP was polymerized with five commercial dianhydrides to give polyimide films. GPC gave Mn of 3.17–4.68 × 104 and Mw of 4.51–7.94 × 104 Da. These amorphous polyimides, with d-spacings of 4.70–5.49 Å, were mostly soluble in polar aprotic solvents. Water contact angles were 83.3–98.6°, with a minimum water absorption of 0.36% after 48 h. Tg ranged from 164 to 211 °C, the maximum T10 was 451 °C under N2, cutoff wavelengths were 353–388 nm, and maximum T450 of 83.6% and maximum T500 of 86.1%. The HEN skeleton contributes to improved solubility, reduced water absorption and enhanced transparency, likely by weakening CTC interactions and loosening chain packing, as reflected by the enlarged interchain d-spacing, although the extent depends on the dianhydride structure. This work suggests that renewable semi-alicyclic polyimides are potential candidates for microelectronic and optoelectronic applications.

Related

  1. Asymmetric synthesis of azabicyclo[2.1.1]hexanes via electrochemical haloamination of methylenecyclobutanes
    Jyothirlatha V. N. Kasu, Tushar Singha, Durga Prasad Hari
    Nature CommunicationsPeer-reviewedCC BY-NC-ND 4.0Full textOrganic chemistryCrossref
  2. Asymmetric total synthesis of veraflorizine, peimine and peiminine
    Hui Wang, Hao Shao, Junjie Chen +4
    Nature CommunicationsPeer-reviewedCC BY-NC-ND 4.0Full textOrganic chemistryCrossref
  3. Convergent Approach for the Asymmetric Synthesis of Vinyl Sulfoximines via Ruthenium-Catalyzed Enantioselective Alkylation of Sulfenamides with (Diazomethyl)phosphonates
    Zachary W. Boyer, Christopher W. Smith, Jonathan A. Ellman
    Organic lettersPeer-reviewedLicence not statedFull textOrganic chemistryPMC
  4. Visible Light‐Driven Copper‐Catalyzed Asymmetric Synthesis via Sequential C(sp 3 )─C(sp 3 ) Bond Scission
    Zhiyong Chi, Boxuan Yang, Xiaoling Cheng +2
    Angewandte Chemie International EditionPeer-reviewedLicence not statedFull text6 citedOrganic chemistryOpenAlex
  5. Rhodium‐Catalyzed Synthesis of Enantioenriched α‐Substituted Primary Amines Through Asymmetric Transfer Hydrogenation
    Chonghuo Liu, Guillaume Lefèvre, Qin Yin +2
    Chemistry (Weinheim an Der Bergstrasse, Germany)Peer-reviewedCC BY 4.0Full text1 citedInorganic & organometallic chemistryPMC

Cite

BibTeXRIS
BibTeX
@article{xiong2026synthesis,
  title = {{Synthesis and Properties of Semi-Alicyclic Polyimides Based on an Asymmetric Diamine from Renewable Menthofuran}},
  author = {Lei Xiong and Xuwen Sun and Tao Yuan and Bing Xiong and Yanxiang Mao and Haixia Qi and Feng Liu},
  journal = {Polymers},
  year = {2026},
  month = nov,
  doi = {10.3390/polym18212771},
  url = {https://www.mdpi.com/2073-4360/18/21/2771},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Synthesis and Properties of Semi-Alicyclic Polyimides Based on an Asymmetric Diamine from Renewable Menthofuran
AU  - Lei Xiong
AU  - Xuwen Sun
AU  - Tao Yuan
AU  - Bing Xiong
AU  - Yanxiang Mao
AU  - Haixia Qi
AU  - Feng Liu
PY  - 2026
DA  - 2026/11/06
JO  - Polymers
DO  - 10.3390/polym18212771
UR  - https://www.mdpi.com/2073-4360/18/21/2771
AB  - Conventional aromatic polyimides suffer from poor solubility, high water absorption and low visible-light transmittance due to strong interchain charge transfer complex (CTC) interactions, limiting their microelectronic and optoelectronic applications. Here, a novel asymmetric bio-based diamine ENDAP bearing a 3,4,5,6,7,8-hexahydro-2H-2,4a-epoxynaphthalene-3,4-diyl (HEN) alicyclic skeleton was synthesized from menthofuran via a four-step route. ENDAP was polymerized with five commercial dianhydrides to give polyimide films. GPC gave Mn of 3.17–4.68 × 104 and Mw of 4.51–7.94 × 104 Da. These amorphous polyimides, with d-spacings of 4.70–5.49 Å, were mostly soluble in polar aprotic solvents. Water contact angles were 83.3–98.6°, with a minimum water absorption of 0.36% after 48 h. Tg ranged from 164 to 211 °C, the maximum T10 was 451 °C under N2, cutoff wavelengths were 353–388 nm, and maximum T450 of 83.6% and maximum T500 of 86.1%. The HEN skeleton contributes to improved solubility, reduced water absorption and enhanced transparency, likely by weakening CTC interactions and loosening chain packing, as reflected by the enlarged interchain d-spacing, although the extent depends on the dianhydride structure. This work suggests that renewable semi-alicyclic polyimides are potential candidates for microelectronic and optoelectronic applications.
SN  - 2073-4360
ER  -