Dye labeled aromatic azides for multi-photon grafting

Katharina Gallas; Dominik Wohlmuth; Zhiquan Li; Aliasghar Ajami; Aleksandr  Ovsianikov; Robert Liska; Christian Slugovc

doi:10.1007/s00706-022-03022-7

Dye labeled aromatic azides for multi-photon grafting

Katharina Gallas, Dominik Wohlmuth, Zhiquan Li, Aliasghar Ajami, Aleksandr Ovsianikov, Robert Liska, Christian Slugovc^*

^*Corresponding author for this work

Institute for Chemistry and Technology of Materials (6380)

Research output: Contribution to journal › Article › peer-review

Abstract

The synthesis of two dye-labeled azides via de-symmetrization of 2,6-bis(4-azidobenzylidene)-4-methylcyclohexanone (BAC-M) with a copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) using fluorescent dyes is reported. An alkyne functionalized dansyl derivative and an alkyne functionalized perylene diimide derivative were used as the dyes. The photo-physical properties of these dye dyads are described, and their performance in multi-photon grafting onto polyethylene glycol-based hydrogels is investigated. While the dansyl-conjugated BAC derivate is well suited for multi-photon grafting with lasers operating at 800 nm, the perylene diimide-bearing dye does not give the desired result. Graphical abstract: [Figure not available: see fulltext.]

Original language	English
Journal	Monatshefte für Chemie - Chemical Monthly
Early online date	13 Dec 2022
DOIs	https://doi.org/10.1007/s00706-022-03022-7
Publication status	E-pub ahead of print - 13 Dec 2022

Keywords

Alkyne-azide cycloaddition
Aromatic azides
Multi-photon absorption
Photo-grafting

ASJC Scopus subject areas

Chemistry(all)

Fields of Expertise

Advanced Materials Science

Access to Document

10.1007/s00706-022-03022-7Licence: CC BY 4.0

Cite this

@article{a79214fa506c475197e5a360ebcf64bb,

title = "Dye labeled aromatic azides for multi-photon grafting",

abstract = "The synthesis of two dye-labeled azides via de-symmetrization of 2,6-bis(4-azidobenzylidene)-4-methylcyclohexanone (BAC-M) with a copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) using fluorescent dyes is reported. An alkyne functionalized dansyl derivative and an alkyne functionalized perylene diimide derivative were used as the dyes. The photo-physical properties of these dye dyads are described, and their performance in multi-photon grafting onto polyethylene glycol-based hydrogels is investigated. While the dansyl-conjugated BAC derivate is well suited for multi-photon grafting with lasers operating at 800 nm, the perylene diimide-bearing dye does not give the desired result. Graphical abstract: [Figure not available: see fulltext.]",

keywords = "Alkyne-azide cycloaddition, Aromatic azides, Multi-photon absorption, Photo-grafting",

author = "Katharina Gallas and Dominik Wohlmuth and Zhiquan Li and Aliasghar Ajami and Aleksandr Ovsianikov and Robert Liska and Christian Slugovc",

year = "2022",

month = dec,

day = "13",

doi = "10.1007/s00706-022-03022-7",

language = "English",

journal = "Monatshefte f{\"u}r Chemie - Chemical Monthly",

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publisher = "Springer Wien",

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TY - JOUR

T1 - Dye labeled aromatic azides for multi-photon grafting

AU - Gallas, Katharina

AU - Wohlmuth, Dominik

AU - Li, Zhiquan

AU - Ajami, Aliasghar

AU - Ovsianikov, Aleksandr

AU - Liska, Robert

AU - Slugovc, Christian

PY - 2022/12/13

Y1 - 2022/12/13

N2 - The synthesis of two dye-labeled azides via de-symmetrization of 2,6-bis(4-azidobenzylidene)-4-methylcyclohexanone (BAC-M) with a copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) using fluorescent dyes is reported. An alkyne functionalized dansyl derivative and an alkyne functionalized perylene diimide derivative were used as the dyes. The photo-physical properties of these dye dyads are described, and their performance in multi-photon grafting onto polyethylene glycol-based hydrogels is investigated. While the dansyl-conjugated BAC derivate is well suited for multi-photon grafting with lasers operating at 800 nm, the perylene diimide-bearing dye does not give the desired result. Graphical abstract: [Figure not available: see fulltext.]

AB - The synthesis of two dye-labeled azides via de-symmetrization of 2,6-bis(4-azidobenzylidene)-4-methylcyclohexanone (BAC-M) with a copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) using fluorescent dyes is reported. An alkyne functionalized dansyl derivative and an alkyne functionalized perylene diimide derivative were used as the dyes. The photo-physical properties of these dye dyads are described, and their performance in multi-photon grafting onto polyethylene glycol-based hydrogels is investigated. While the dansyl-conjugated BAC derivate is well suited for multi-photon grafting with lasers operating at 800 nm, the perylene diimide-bearing dye does not give the desired result. Graphical abstract: [Figure not available: see fulltext.]

KW - Alkyne-azide cycloaddition

KW - Aromatic azides

KW - Multi-photon absorption

KW - Photo-grafting

UR - http://www.scopus.com/inward/record.url?scp=85143889583&partnerID=8YFLogxK

U2 - 10.1007/s00706-022-03022-7

DO - 10.1007/s00706-022-03022-7

M3 - Article

JO - Monatshefte für Chemie - Chemical Monthly

JF - Monatshefte für Chemie - Chemical Monthly

SN - 0026-9247

ER -

Dye labeled aromatic azides for multi-photon grafting

Abstract

Keywords

ASJC Scopus subject areas

Fields of Expertise

Access to Document

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