Related Experiment Video
Updated: Jun 27, 2026
09:37
Cellular Encapsulation in 3D Hydrogels for Tissue Engineering
Published on: October 26, 2009
36.9K
A Comparative Study between Thiol-Ene and Acrylate Photocrosslinkable Hyaluronic Acid Hydrogel Inks for Digital Light
Therese Steudter1,2, Tobias Lam3, Hamidreza Pirmahboub3
1INM - Leibniz Institute for New Materials, 66123, Saarbrücken, Germany.
Macromolecular Bioscience
|December 31, 2024
Summary
Thiol-ene hyaluronic acid (HA) hydrogels offer superior precursor stability and faster photocrosslinking than methacrylate HA. This enables high-resolution bioprinting with improved control over network formation.
Area of Science:
- Biomaterials Science
- Polymer Chemistry
- Bioprinting Technologies
Background:
- Photocrosslinkable hydrogels are crucial for light-based fabrication and bioprinting.
- Thiol-ene reactions are proposed as superior alternatives to methacrylate chemistries for hydrogel formation.
- Hyaluronic acid (HA) is a key biomaterial for tissue engineering and regenerative medicine applications.
Purpose of the Study:
- To quantitatively compare thiol-ene and methacrylate crosslinked hyaluronic acid (HA) hydrogels.
- To evaluate precursor stability, photocrosslinking control, and printing resolution for bioprinting applications.
- To assess the benefits of thiol-ene functionalization for HA-based inks.
Main Methods:
- Synthesis of HA functionalized with norbornene, allyl ether, or methacrylate groups.
- Storage stability testing of functionalized HA precursors.
- Photorheology to analyze photocrosslinking kinetics and network formation.
- Digital Light Processing (DLP) bioprinting to determine feature resolution.
Main Results:
- Thiol-ene HA precursors exhibited 3.8 times greater storage stability than methacrylated HA.
- Photocrosslinking was up to 4.7 times faster with thiol-ene HA, offering better temporal control.
- DLP printing of 4% w/v HA hydrogels achieved 100 µm feature resolution in 2 seconds.
- This represents the smallest feature size reported for DLP printing using HA-based thiol-ene hydrogels.
Conclusions:
- Thiol-ene chemistry provides significant advantages over methacrylate chemistry for HA-based hydrogel bioprinting.
- Enhanced precursor stability and rapid, controlled photocrosslinking are key benefits.
- The findings support the synthetic effort required for thiol-ene functionalization for advanced bioprinting.
Keywords:
digital light processinginkphotocrosslinkable hydrogelstereolithographythiol‐ene crosslinkingMore Related Videos
Related Concept Videos
01:28IR and UV–Vis Spectroscopy of Carboxylic Acids
In IR spectroscopy of carboxylic acids, the C=O bond shows a characteristic band between 1710 and 1760 cm⁻¹, and the O–H bond exhibits a broad band between 2500 and 3300 cm⁻¹.
However, the stretching absorptions for the C=O bond vary depending on the structure of carboxylic acids. The C=O bond of the free carboxylic acids shows a higher stretching frequency, 1760 cm−1, while H-bonded carboxylic acids (dimers) exhibit stretching absorptions at a lower frequency, 1710 cm−1. The C=O bond of the...
However, the stretching absorptions for the C=O bond vary depending on the structure of carboxylic acids. The C=O bond of the free carboxylic acids shows a higher stretching frequency, 1760 cm−1, while H-bonded carboxylic acids (dimers) exhibit stretching absorptions at a lower frequency, 1710 cm−1. The C=O bond of the...
01:26Spectroscopy of Carboxylic Acid Derivatives
Infrared spectroscopy is primarily used to determine the types of bonds and functional groups. In carboxylic acid derivatives, a typical carbonyl bond absorption is observed around 1650–1850 cm−1. For esters, the absorption is recorded at around 1740 cm−1, while acid halides show the absorption at about 1800 cm−1. Another acid derivative, the acid anhydrides, exhibit two carbonyl absorption around 1760 cm−1 and 1820 cm−1, arising from the symmetrical and unsymmetrical carbonyl vibration.
In the...
In the...
01:19Physical Properties of Carboxylic Acid Derivatives
Intermolecular forces dictate several physical properties such as boiling points, melting points, solubilities, and so forth. They are classified into four types: ionic forces, hydrogen bonds, dipole–dipole forces, and dispersion forces. Ionic forces are the strongest, while dispersion forces are the weakest.
Among the carboxylic acid derivatives, the boiling points of acid chlorides and esters are very similar and are the lowest in the series. Acid anhydrides have slightly higher boiling...
Among the carboxylic acid derivatives, the boiling points of acid chlorides and esters are very similar and are the lowest in the series. Acid anhydrides have slightly higher boiling...
01:31Physical Properties of Carboxylic Acids
Carboxylic acids with lower molecular weight exhibit a sharp and unpleasant odor. They also have higher boiling and melting points than analogous compounds, such as aldehydes, ketones, and alcohols.