Tetraphenylethylene‐Interweaving Conjugated Macrocycle Polymer Materials as Two‐Photon Fluorescence Sensors for Metal Ions and Organic Molecules

• Published in: Advanced materials (Weinheim) Vol. 30; no. 20; pp. e1800177 - n/a
• Main Authors: Li, Xi, Li, Zheng, Yang, Ying‐Wei
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 01.05.2018
• Subjects: Aromatic compounds; Carcinogens; conjugated polymers; Coupling (molecular); Fluorescence; Materials science; Molecular chains; Organic chemistry; Organic compounds; pillararenes; Polymers; sensing; supramolecular chemistry; two‐photon fluorescence; sensing; two-photon fluorescence; supramolecular chemistry; pillararenes; conjugated polymers
• ISSN: 0935-9648; 1521-4095; 1521-4095
• DOI: 10.1002/adma.201800177

A luminescent conjugated macrocycle polymer (CMP) with strong two‐photon fluorescence property, namely, P[5]‐TPE‐CMP, is constructed from ditriflate‐functionalized pillar[5]arene and a 1,1,2,2‐tetrakis(4‐ethynylphenyl)ethylene (TPE) linker through a Sonogashira–Hagihara cross‐coupling reaction. Significantly, in sharp contrast with the corresponding conjugated microporous polymer without synthetic macrocycles, P[5]‐TPE‐CMP shows an outstanding stability against photobleaching and exhibits highly selective cation sensing capability toward Fe3+ at different excitation wavelengths (both UV and red–near‐infrared regions). Meanwhile, its fluorescence could also be sufficiently quenched by 4‐amino azobenzene, a frequently used organic dye that is certified to be carcinogenic, as compared with a group of common organic compounds. This work paves a new way for enhancing the properties of porous organic polymers through the introduction of supramolecular macrocycles like macrocyclic arenes. Conjugated macrocycle polymers are first constructed from ditriflate‐functionalized pillararene and a 1,1,2,2‐tetrakis(4‐ethynylphenyl)ethylene linker through a Sonogashira–Hagihara cross‐coupling reaction. They show excellent two‐photon fluorescence (TPF) and serve as a highly efficient TPF sensor for metal ions and organic molecules.