Forbidden Chemistry: Two-Photon Pathway in [2+2] Cycloaddition of Maleimides
Publikation: Beitrag in Fachzeitschrift › Forschungsartikel › Beigetragen › Begutachtung
Beitragende
Abstract
Two-photon excitation provides high spatial resolution in three dimensions of the corresponding chemical or physical processes, allowing submicrometer structuring in stereolithography and three-dimensional (3D) microfabrication. While studying two-photon structuring applications, we observed an undescribed phenomenon in photochemistry that dictates reactivity of maleimide groups in two-photon mode. A low-absorbance transition formerly ignored in classical photochemistry has been found for maleimides. This transition was assigned to symmetry-breaking donor-acceptor complex formation, which revealed a formally forbidden pathway in [2+2] cycloaddition reactions of maleimide moieties. This synthetic pathway allowed for the creation of hydrogel materials under physiological conditions at low laser excitation energy (0.1 J/cm2 at 800 nm) without the use of photoinitiators, which makes it truly two-photon click chemistry.
Details
Originalsprache | Englisch |
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Seiten (von - bis) | 10184-10187 |
Seitenumfang | 4 |
Fachzeitschrift | Journal of the American Chemical Society |
Jahrgang | 139 |
Ausgabenummer | 30 |
Publikationsstatus | Veröffentlicht - 6 Juli 2017 |
Peer-Review-Status | Ja |
Externe IDs
PubMed | 28682611 |
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ORCID | /0000-0002-6209-2364/work/142237672 |
ORCID | /0000-0003-0189-3448/work/159607179 |