Author, as appears in the article.: Choo YSL; Giamberini M; Antonio J; Waddell PG; Benniston AC

Department: Química Analítica i Química Orgànica Enginyeria Química

e-ISSN: 1477-0539

URV's Author/s: Giamberini, Marta / Reina Lozano, José Antonio

Abstract: © 2020 The Royal Society of Chemistry. The reaction of diethyl 2,5-bis(tert-butyl)phenoxy-3,6-dihydroxyterephthalate (1) with tetraethylene glycol di(p-toluenesulfonate) under high-dilution conditions afforded several isolated products. Two products were identified as macrocycles with one being the 1 + 1 crown ether derivative 3 (10% yield), and the second being the 2 + 2 crown ether compound D3 (19% yield). The X-ray structure for 3 was determined with the asymmetric unit observed to comprise half of the molecule. The small crown ether ring of 3 interacts with K+ or H+ ions in MeOH, but binding is weak and the macrocyclic cavity is too small to fully encapsulate the K+ ion. Transesterification of compounds 1, its methylated version 2 and 3 with diols such as ethylene glycol or 1,4-butandiol produced monomers (M1-M3) which were reacted with terephthaloyl chloride. Short oligomers were produced (PolyM1-PolyM3) rather than extensive polymeric materials and all displayed solid state fluorescence. The absorption and fluorescence properties of M1-M2 and their polymers can be related to subtle structural changes. The Stokes shift for M2 of 15 627 cm-1 in DCM is one of the largest observed for a simple organic chromophore in fluid solution.

Thematic Areas: Química Physical and theoretical chemistry Organic chemistry Odontología Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, organic Biotecnología Biodiversidade Biochemistry

licence for use: https://creativecommons.org/licenses/by/3.0/es/

ISSN: 1477-0520

Author's mail: joseantonio.reina@urv.cat marta.giamberini@urv.cat

Author identifier: 0000-0002-9245-4135 0000-0001-8278-3552

Record's date: 2023-02-19

Papper version: info:eu-repo/semantics/publishedVersion

Link to the original source: https://pubs.rsc.org/en/content/articlelanding/2020/ob/d0ob01533d#!divAbstract

Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/

Papper original source: Organic & Biomolecular Chemistry. 18 (42): 8735-8745

APA: Choo YSL; Giamberini M; Antonio J; Waddell PG; Benniston AC (2020). Functionalized fluorescent terephthalate monomers and their attempted polyester formation. Organic & Biomolecular Chemistry, 18(42), 8735-8745. DOI: 10.1039/d0ob01533d

Article's DOI: 10.1039/d0ob01533d

Entity: Universitat Rovira i Virgili

Journal publication year: 2020

Publication Type: Journal Publications