Approaches to the Functionalization of Organosilicon Dendrones Based on Limonene

Round 1

Reviewer 1 Report

The manuscript describes the use of limonene, which is a renewable resource as a building block for the synthesis of silicon-containing dendrimer building blocks. It is an interesting idea and it will be interesting to see, where it leads to in the future. Nice work!

Author Response

Thank you for high evaluation of our article and for your hard work in reviewing!

We will certainly work on this field further, since it is the topic of our PhD student. We will publish new results as soon as we get them.

Reviewer 2 Report

The manuscript is straightforward and could be accepted for publication.

Some minor remarks:

i) The use of English language should be checked in some cases.

ii) The introductory paragraphs (lines 210-232) are really necessary, here? 

iii) Section 3.3. Was somehow verified the success of the reactions reported in this section?

Author Response

1. Thank you for reading our manuscript thoroughly. We checked and revised some mistakes and typos.
2. We have inserted this paragraph so that the reader understands the reason for using limonene as a natural compound for the synthesis of carbosilane dendrons. The fact is that similar dendrons were previously obtained in our laboratory. However, the use of limonene in this case is justified, since its use allows the use of two double bonds in series for dendron growth and functionalization of the focal point. In our previous article [https://doi.org/10.3390/polym14163279], the reviewers had questions about the logic of choosing just such a synthesis strategy. Therefore, we decided to give a more detailed description in this article.
3. All the products were investigated by NMR and GPC as others. We inserted in the text the phrase: The structure and purity of the dendrons was confirmed by NMR spectroscopy and GPC (Supporting Information, SI1 and SI2)

 

Reviewer 3 Report

This manuscript continues studies on carbosilane and carbosiloxane dendrimers that the researchers have been engaged in for quite some time.  The experimental is clear, with reference to previous work and the products are reasonably well-characterized.  While there are no surprises in the report, the paper represents good incremental progress of the research.  It is not fragmentary, as it presents a logical place to report, though I do hope to see a report on the azide alkyne ‘click’ of the azide core and the propiolate core in future plans.   It is unfortunate that the reactions give mixtures of regioisomers and stereosiomers, but that is not a barrier to publication.  The English is reasonable, but there are some issue that I would recommend to enhance the readability of the manuscript:

 

1.     There are missing references in the first entries of the materials and methods sections.

2.     It takes the reader some unnecessary effort to make sense of the stersoisomers and regioisomers formed during the openings of the epoxides.  I would suggest that the figures be revised to show stereochemistry at all points.  While the stereochemistry has not been rigorously established in the study, I think there is ample precedent to indicate the structures with confidence.

3.     I think that it is worth stating that the core is D-limonene, the naturally occurring material.  While it likely goes without saying, it would be nice to confirm the starting material.  No need to state it for every compound but a single line that the starting material is chiral would be nice.

I found this an interesting paper and I  enjoyed reading it.

Author Response

1. Thank you for carefully reading of the manuscript. It is strange, because in .doc format all references look correct. Maybe it is some problems with convertation in .pdf format.
2. Thanks for your comment! The point is that in this work, the very fact of the formation of isomers is unimportant to us. In the case of dendrimers, the absolute configuration is not important, since it does not affect their physical properties. However, to understand the fact that several signals appear in the NMR spectra, determined by the presence of the racemate, requires a visual explanation.
3. Thank you for your comment! We inserted explanation in the text (mark yellow).