Controlling the Degree of Functionalization: In-Depth Quantification and Side-Product Analysis of Diazonium Chemistry
Milan Schirowski1,2, Frank Hauke1,2, Andreas Hirsch1,2
1Joint Institute of Advanced Materials and Processes (ZMP), Friedrich-Alexander University of Erlangen-Nürnberg, Dr.-Mack-Str. 81, 90762, Fürth, Germany.
Abstract:
We present an in-depth qualitative and quantitative analysis of a reaction between 4-iodobenzenediazonium tetrafluoroborate and single-walled carbon nanotubes (SWCNTs) via thermogravimetric analysis coupled with mass spectrometry (TG-MS) or a gas chromatography and mass spectrometry (TG-GC-MS) as well as Raman spectroscopy. We propose a method for precise determination of the degree of functionalization and quantification of physisorbed aromates, detaching around their boiling point, alongside covalently bonded ones (cleavage over 200 °C). While the presence of some side products like phenol- or biphenyl species could be excluded, residual surfactant and minor amounts of benzene could be identified. A concentration-dependent experiment shows that the degree of functionalization increases with the logarithm of the concentration of applied diazonium salt, which can be exploited to precisely adjust the amount of aryl addends on the nanotube sidewall, up to 1 moiety per 100 carbon atoms.
Related Concept Videos
Diazonium Group Substitution: –OH and –H
One-Degree-of-Freedom System
A one-degree-of-freedom system is defined by an independent variable that determines its state and behavior. One example of a one-degree-of-freedom system is a simple harmonic oscillator, such as a...
Degrees of Freedom
For example, suppose there are three unknown numbers whose mean is 10; although we can freely assign values to the first and second numbers, the value of the last number can not be arbitrarily assigned.
Degrees of Freedom
For example, suppose there are three unknown numbers whose mean is 10; although we can freely assign values to the first and second numbers, the value of the last number can not be arbitrarily...
Degree of Unsaturation
The degree of unsaturation for hydrocarbons is U = (2C + 2 − H) / 2, where C is the number of carbon atoms and H is the number of hydrogen atoms.
Transfer Function in Control Systems
To derive the transfer function, consider a general nth-order linear time-invariant...


