Synthesis and Characterization of New Potential Hypoxia-Sensitive Azo-thiacalix[4]arenes Derivatives
, Ekaterina S. Churbanova 2, Mohamed A. Khalifa 2,3, Sofia R. Kleshnina 1, Svetlana E. Solovieva 1,2 and Igor S. Antipin 1,2Round 1
Reviewer 1 Report
The paper is interesting and it is worth of publication if the authors could conveniently address the following issues:
1. Editing of English language and style are required
2. Line 66: The “p” of p-nitroaniline should be in italic.
3. Line 76: change “25,26,27,28-Tetrakis(p-bromalkoxy)-5,11,17,23-tetra(tert-butyl)thiacalix[4]aren” to “25,26,27,28-Tetrakis(p-bromalkoxy)-5,11,17,23-tetra(tert-butyl)thiacalix[4]arene”.
4. Line 77: According to the SI Units System, the symbol for litre is the uppercase letter L.
5. Lines 64, 84, 87, 96, 99: Conventionally, in the case of deuterated solvents, the notation “d” is in lowercase letter and italicized.
6. The NMR proton signals of p-substituted benzenes are often incorrectly described as doublets, because the resolution of the spectrum is not high enough, or because sometimes it looks simply like a doublet. The NMR spectrum of p-substituted benzenes are a classic example of AA’XX’ splitting patterns and, therefore, once the various coupling constants could not be obtained, the observed signals for the aromatic protons should more correctly be described as an apparent doublet (app d) without mentioning any J value.
Author Response
We are grateful to the reviewer for their constructive remarks, comments and suggestions. We've revised our manuscript according to their recommendations. The changes are marked up using the “Track Changes” function in the revised version of the manuscript. Below is also our detailed point-by-point response.
Comments and Suggestions from Reviewer 1.
- Editing of English language and style are required
Done. We thank referee for his/her comment. The appropriate correction has been done in the revised version of the manuscript.
- Line 66: The “p” of p-nitroaniline should be in italic.
Done.
- Line 76: change “25,26,27,28-Tetrakis(p-bromalkoxy)-5,11,17,23-tetra(tert-butyl)thiacalix[4]aren” to “25,26,27,28-Tetrakis(p-bromalkoxy)-5,11,17,23-tetra(tert-butyl)thiacalix[4]arene”.
Done.
- Line 77: According to the SI Units System, the symbol for litre is the uppercase letter L.
Done.
- Lines 64, 84, 87, 96, 99: Conventionally, in the case of deuterated solvents, the notation “d” is in lowercase letter and italicized.
Done.
- The NMR proton signals of p-substituted benzenes are often incorrectly described as doublets, because the resolution of the spectrum is not high enough, or because sometimes it looks simply like a doublet. The NMR spectrum of p-substituted benzenes are a classic example of AA’XX’ splitting patterns and, therefore, once the various coupling constants could not be obtained, the observed signals for the aromatic protons should more correctly be described as an apparent doublet (app d) without mentioning any J value.
Done. We thank referee for his/her comment. The appropriate correction has been done in the revised version of the manuscript.
Reviewer 2 Report
The azo-thiacalix[4]arenes derivatives were synthesized and characterized by 1H and 13C NMR, IR spectroscopy, MALDI TOF mass spectrometry, and elemental analysis. A highly productive method for the synthesis of thiacalixarene with four anionic sulphonate azo fragments on the lower rim for further complexation with cationic dyes is reported. The synthesis and characterization are doing well down.
We are looking forward the results of these compounds on the hypoxia sensitive.
Author Response
We are grateful to the reviewer for their time and appreciation of our work.
Reviewer 3 Report
This Communication describes the synthesis of two new potential hypoxia-sensitive azo-thiacalix[4]arenes derivatives in the 1,3-alternate configuration. The authors report а new highly productive method for the synthesis of two thiacalixarenes with four anionic sulphonate azo fragments and their further complexation with cationic dyes. The compounds are well described and properly characterized by using IR, NMR, MALDI TOF, and elemental analysis measurements.
I recommend this Communication for publication in Molbank.
Author Response
We are grateful to the reviewer for their time and appreciation of our work.
