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Hierarchically Templated Synthesis of 3D‐Printed Crosslinked Cyclodextrins for Lycopene Harvesting

Journal Article · · Small
Abstract

Plants produce a wide range of bioactive phytochemicals, such as antioxidants and vitamins, which play crucial roles in aging prevention, inflammation reduction, and reducing the risk of cancer. Selectively harvesting these phytochemicals, such as lycopene, from tomatoes through the adsorption method is cost‐effective and energy efficient. In this work, a templated synthesis of 3D‐printed crosslinked cyclodextrin polymers featuring nanotubular structures for highly selective lycopene harvesting is reported. Polypseudorotaxanes formed by triethoxysilane‐based telechelic polyethylene glycols and α‐cyclodextrins (α‐CDs) are designed as the template to (1) synthetically access urethane‐based nanotubular structures at the molecular level, and (2) construct 3D‐printed architectures with designed macroscale voids. The polypseudorotaxane hydrogels showed good rheological properties for direct ink writing, and the 3D‐printed hydrogels were converted to the desired α‐CD polymer network through a three‐step postprinting transformation. The obtained urethane‐crosslinked α‐CD monoliths possess nanotubular structures and 3D‐printed voids. They selectively adsorb lycopene from raw tomato juice, protecting lycopene from photo‐ or thermo‐degradations. This work highlights the hierarchically templated synthesis approach in developing functional 3D‐printing materials by connecting the bottom‐up molecular assembly and synthesis with the top‐down 3D architecture control and fabrication.

Sponsoring Organization:
USDOE
Grant/Contract Number:
SC0022267
OSTI ID:
1968970
Alternate ID(s):
OSTI ID: 2575936
Journal Information:
Small, Journal Name: Small; ISSN 1613-6810
Publisher:
Wiley Blackwell (John Wiley & Sons)Copyright Statement
Country of Publication:
Germany
Language:
English

References (43)

Supramolecular network formation through inclusion complexation of an α-cyclodextrin-based molecular tube journal November 2000
3D Printed Multifunctional, Hyperelastic Silicone Rubber Foam journal April 2019
Cyclodextrin Inclusion Compounds in Research and Industry journal May 1980
Ring Shuttling Controls Macroscopic Motion in a Three-Dimensional Printed Polyrotaxane Monolith journal March 2017
Advanced Polymer Designs for Direct‐Ink‐Write 3D Printing journal July 2019
Phytochemicals journal October 1997
Lycopene degradation and isomerization in tomato dehydration journal January 1999
Complexation of phytochemicals with cyclodextrin derivatives – An insight journal April 2017
Complexation of phytochemicals with cyclodextrins and their derivatives- an update journal May 2022
Preparation and adsorption property of chitosan beads bearing β-cyclodextrin cross-linked by 1,6-hexamethylene diisocyanate journal May 2008
Kinetic trapping of 3D-printable cyclodextrin-based poly(pseudo)rotaxane networks journal September 2021
Analytical tools for the analysis of carotenoids in diverse materials journal February 2012
Preparative separation and purification of lycopene from tomato skins extracts by macroporous adsorption resins journal December 2010
Long-term stability of food-grade nanoemulsions from high methoxyl pectin containing essential oils journal January 2016
Environmental applications of water-insoluble β-cyclodextrin–epichlorohydrin polymers journal February 2013
Separation and identification of carotenoids and their oxidation products in the extracts of human plasma journal September 1992
Chemical Stability of Lycopene in Processed Products: A Review of the Effects of Processing Methods and Modern Preservation Strategies journal December 2019
Introduction and General Overview of Cyclodextrin Chemistry journal July 1998
Phytochemicals for Health, the Role of Pulses journal September 2007
Two-Phase Channel Structures Based on α-Cyclodextrin−Polyethylene Glycol Inclusion Complexes journal September 2004
α-Cyclodextrin/Polyethylene Glycol Polyrotaxane:  A Study of the Threading Process journal April 1997
Nucleation Mechanism of α-Cyclodextrin-Enhanced Crystallization of Some Semicrystalline Aliphatic Polymers journal August 2005
Synthesis of a Molecular Tube in Dimethyl Sulfoxide and Its Inclusion Complexation Behavior with Poly(ethylene oxide-ran-propylene oxide) journal June 2008
The molecular necklace: a rotaxane containing many threaded α-cyclodextrins journal March 1992
Synthesis of a tubular polymer from threaded cyclodextrins journal August 1993
Rapid removal of organic micropollutants from water by a porous β-cyclodextrin polymer journal December 2015
An artificial molecular pump journal May 2015
Aligned macrocycle pores in ultrathin films for accurate molecular sieving journal August 2022
Thermomechanical properties, antibiotic release, and bioactivity of a sterilized cyclodextrin drug delivery system journal January 2014
Rapid macroscale shape morphing of 3D-printed polyrotaxane monoliths amplified from pH-controlled nanoscale ring motions journal January 2018
Cyclodextrin embedded covalently crosslinked networks: synthesis and applications of hydrogels with nano-containers journal January 2020
3D printing of cellular materials for advanced electrochemical energy storage and conversion journal January 2020
Advanced supramolecular design for direct ink writing of soft materials journal January 2023
Temperature dependence of inclusion-dissociation behavior between molecular nanotubes and linear polymers journal January 2001
Atomic force microscopy observation of insulated molecular wire formed by conducting polymer and molecular nanotube journal February 2002
Inclusion behavior between molecular nanotubes and linear polymer chains in aqueous solutions journal March 2000
Lycopene: Chemistry, Biology, and Implications for Human Health and Disease journal April 2009
A precise polyrotaxane synthesizer journal June 2020
Manipulation of Insulated Molecular Wire with Atomic Force Microscope
  • Tomonori Akai, Tomonori Akai; Takumi Abe, Takumi Abe; Takeshi Shimomura, Takeshi Shimomura
  • Japanese Journal of Applied Physics, Vol. 40, Issue 12A https://doi.org/10.1143/JJAP.40.L1327
journal December 2001
Thermal stability, antioxidant activity, and photo-oxidation of natural polyphenols journal January 2014
Phytochemicals in Cancer Treatment: From Preclinical Studies to Clinical Practice journal January 2020
Comparative Evaluation of Solubility, Cytotoxicity and Photostability Studies of Resveratrol and Oxyresveratrol Loaded Nanosponges journal October 2019
Lycopene - A Review: Chemistry, Source, Health Role, Extraction, Applications journal March 2022

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