Issue 44, 2019

Thiol–yne chemistry for 3D printing: exploiting an off-stoichiometric route for selective functionalization of 3D objects

Abstract

An alkyne monomer bis(propargyl) fumarate is synthesized and used to produce DLP-3D printable formulations with a thiol exploiting photoinduced thiol–yne reaction. By preparing mixtures containing different relative ratios of two monomers, it is possible to obtain polymers exposing different unreacted functional groups on their surface. The reactivity of the formulations toward visible light irradiation is studied by ATR analysis and photorheology tests, the printability with DLP equipment is demonstrated and the thermomechanical properties of the obtained polymers are investigated by DMA. Changing the printing formulation during the printing process, objects exposing either triple bonds or thiol groups or a mix of them can be obtained, and the presence of unreacted groups is confirmed by XPS analysis; this property can be exploited to selectively functionalize the built parts in a dedicated post process. As a proof of concept, a simple hybrid structure is treated with an azide-terminated squaraine dye, to exploit a ‘click’ reaction with the alkyne groups available. The fluorescence of the functionalized structure is observed with a spinning disk confocal microscope. Such a strategy can allow producing 3D objects with a controllable structure just by varying the relative ratio of the co-monomers in the formulations during the printing process.

Graphical abstract: Thiol–yne chemistry for 3D printing: exploiting an off-stoichiometric route for selective functionalization of 3D objects

Supplementary files

Article information

Article type
Paper
Submitted
30 জুন 2019
Accepted
06 সেপ্টে. 2019
First published
06 সেপ্টে. 2019

Polym. Chem., 2019,10, 5950-5958

Thiol–yne chemistry for 3D printing: exploiting an off-stoichiometric route for selective functionalization of 3D objects

I. Roppolo, F. Frascella, M. Gastaldi, M. Castellino, B. Ciubini, C. Barolo, L. Scaltrito, C. Nicosia, M. Zanetti and A. Chiappone, Polym. Chem., 2019, 10, 5950 DOI: 10.1039/C9PY00962K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements