Jump to main content
Jump to site search

Issue 8, 2019
Previous Article Next Article

Synthesis and photophysical properties of conjugated (dodecyl)benzoateethynylene macromolecules: staining of Bacillus subtilis and Escherichia coli rhizobacteria

Author affiliations

Abstract

A series of hydrogen, iodine and triazene terminated (dodecyl)benzoateethynylene oligomers and the homologue polymer were synthesized by a divergent–convergent step-by-step approach and characterized by NMR (1H, 13C, HSQC) and MALDI-TOF mass spectrometry. The photophysical properties in CH2Cl2 were analyzed by UV-vis and static and dynamic fluorescence revealing that all of the materials are semiconducting with good fluorescence quantum yields ϕ and lifetimes in the range of ns. The type of terminal group in the oligomers, H, I or triazene, has an important effect on both absorption and emission properties, with the maximum red shifts for I and triazene and with a larger bathochromic effect for the triazene oligomers. The structural distortion of the conjugated backbone increases with the benzoateethynylene moieties (BzE) in the hydrogen terminated oligomers (trimer, pentamer and heptamer) as found by theoretical simulations, which explains why the saturation of the effective conjugation is found for the heptamer (8 nm with respect to the polymer). The hydrogen terminated pentamer showed the highest quantum yield of the series with ϕ = 77%, is soluble in N-methylpyrrolidone and displays a strong C[triple bond, length as m-dash]C vibration Raman signal. Its application in staining the Gram-positive Bacillus subtilis and Gram-negative Escherichia coli was investigated under in vitro conditions and was successfully demonstrated by fluorescence and microRaman spectroscopy and laser scanning confocal microscopy.

Graphical abstract: Synthesis and photophysical properties of conjugated (dodecyl)benzoateethynylene macromolecules: staining of Bacillus subtilis and Escherichia coli rhizobacteria

Back to tab navigation

Supplementary files

Article information


Submitted
20 Nov 2018
Accepted
18 Jan 2019
First published
21 Jan 2019

New J. Chem., 2019,43, 3332-3340
Article type
Paper

Synthesis and photophysical properties of conjugated (dodecyl)benzoateethynylene macromolecules: staining of Bacillus subtilis and Escherichia coli rhizobacteria

Ma. Concepción García, G. Turlakov, I. Moggio, E. Arias, J. H. Valenzuela, M. Hernández, G. Rodríguez and R. F. Ziolo, New J. Chem., 2019, 43, 3332
DOI: 10.1039/C8NJ05892J

Social activity

Search articles by author

Spotlight

Advertisements