Fluorescent supramolecular hierarchical self-assemblies from glycosylated 4-amino- and 4-bromo-1,8-naphthalimides

Calatrava-Pérez, Elena; Acherman, Stefan; Stricker, Lucas; McManus, Gavin; Delente, Jason; Lynes, Amy D.; Henwood, Adam F.; Lovitt, June I.; Hawes, Chris S.; Byrne, Kevin; Schmitt, Wolfgang; Kotova, Oxana; Gunnlaugsson, Thorfinnur; Scanlan, Eoin M.

Abstract

An investigation into the self-assembly of two 4-amino- and a 4-bromo-1,8-naphthalimide (Nap) based structures (1–3) possessing an appended glycan unit, from protic polar media, is presented. The results demonstrate the formation of complex hierarchical luminescent aggregates, wherein the morphologies, sizes and spherical structures were highly dependent on both the media and the Nap structure. Upon cleaving the native glycosidic bond, using an enzyme, the structure/morphology of the self-assembly of 3 in buffered solution was significantly transformed.

Citation

Calatrava-Pérez, E., Acherman, S., Stricker, L., McManus, G., Delente, J., Lynes, A. D., Henwood, A. F., Lovitt, J. I., Hawes, C. S., Byrne, K., Schmitt, W., Kotova, O., Gunnlaugsson, T., & Scanlan, E. M. (in press). Fluorescent supramolecular hierarchical self-assemblies from glycosylated 4-amino- and 4-bromo-1,8-naphthalimides. Organic and Biomolecular Chemistry, 18(18), 3475-3480. https://doi.org/10.1039/d0ob00033g

• Journal Article Type: Article
• Acceptance Date: Apr 16, 2020
• Online Publication Date: Apr 16, 2020
• Deposit Date: Jun 15, 2023
• Journal: Organic & Biomolecular Chemistry
• Print ISSN: 1477-0520
• Electronic ISSN: 1477-0539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 18
• Issue: 18
• Pages: 3475-3480
• DOI: https://doi.org/10.1039/d0ob00033g
• Keywords: Organic Chemistry; Physical and Theoretical Chemistry; Biochemistry
• Public URL: https://keele-repository.worktribe.com/output/468092
• Additional Information: : This document is Similarity Check deposited; : Supplementary Information; : Crystal Structure Data; : June I. Lovitt (ORCID); : Chris S. Hawes (ORCID); : Wolfgang Schmitt (ORCID); : Oxana Kotova (ORCID); : Oxana Kotova (ResearcherID); : Thorfinnur Gunnlaugsson (ORCID); : Eoin M. Scanlan (ORCID); : Single-blind; : Received 7 January 2020; Accepted 16 April 2020; Accepted Manuscript published 16 April 2020; Advance Article published 24 April 2020; Version of Record published 13 May 2020