5-(9-(p-Tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazol-6-yl)thiophene-2-carbaldehyde

Round 1

Reviewer 1 Report (Previous Reviewer 1)

Comments on revision 1:

-Include mmol also for the product

-Indicate which carbon signals that originate from two carbons e.g.; 126.5 (2C).

-What type of petroleum ether was used (boiling range)?

Author Response

The authors are grateful to the reviewer for a kind and highly professional review.

Point 1.

-Include mmol also for the product

Response from authors.

Corrected as requested by the reviewer.

Point 2.

-Indicate which carbon signals that originate from two carbons e.g.; 126.5 (2C).

Response from authors.

Unfortunately, the authors did not find this entry in the paper.

Point 3.

-What type of petroleum ether was used (boiling range)?

Response from authors.

The boiling range of petroleum ether has been added to the paper.

Reviewer 2 Report (Previous Reviewer 2)

The present revised manuscript by the Knyazeva group describes a synthesis of the revised but novel titled aldehyde compound 2 by using Suzuki-Miyaura cross-coupling.  In the precedent submitted manuscript, the author introduce the new compound prepared by Knoevenagel condensation of with aldehyde 2 with cyanoacetic acid to produce compound NIK231.  Unfortunately, compound NIK231 was sufficiently pure judging from the criteria of Molbank. 

Thus, the author abandoned to report on the synthesis of NIK231, and instead, proposed the synthesis of aldehyde intermediate 2, in which the synthesis and the characterization seem sound and well-implemented.   

Accordingly, the reviewer recommends the publication in Molbank after revisions commented below.

<Comments & suggestions>

1.     Abstract, line 14; ¹H, ¹³C NMR, → ¹H and ¹³C NMRs,    Also, p. 2 line 57.

2.     Abstract, line 14; can → would

3.     Page 2, 45; were isolated → were recovered

4.     Page 3, EtOAc and ethyl acetate are mixed.  Please uniform it.  

Moderate editing of English language required

Author Response

The authors are grateful to the reviewer for a kind and highly professional review.

Point 1.

1. Abstract, line 14; ¹H, ¹³C NMR, → ¹H and ¹³C NMRs,    Also, p. 2 line 57.

Response from authors.

Corrected as requested by the reviewer.

Point 2.

2. Abstract, line 14; can → would

Response from authors.

Corrected as requested by the reviewer.

Point 3.

3. Page 2, 45; were isolated → were recovered

Response from authors.

Corrected as requested by the reviewer.

Point 4.

4. Page 3, EtOAc and ethyl acetate are mixed.  Please uniform it.  

Response from authors.

Corrected as requested by the reviewer.

This manuscript is a resubmission of an earlier submission. The following is a list of the peer review reports and author responses from that submission.

Round 1

Reviewer 1 Report

Checklist:

·         According to the aim and scope of the journal focus is on synthesis. Therefore, the experimental parts on solar cell/characterization should be put in the supporting information file

·         The title could include: Synthesis of

·         The compound is new according to search in Reaxys

·         There are mistakes in the reporting of 13C NMR.

·         The language is at an acceptable level.

·         Schemes and formulas are OK

A problem with this report is that the product/NIK231 dye, as evaluated from NMR spectroscopy is not sufficiently pure. Both in the aliphatic and aromatic region clear signs of impurities are seen. There are also some mistakes in the reported 13C spectra.

Compound 2 contains 24 carbons. Unless there is hindered rotation around the N-tolyl bond this should result in 22 signals. The intensity of signals indicates that there are two pairs of identical carbons.

It should be indicated which carbon signals origin from two carbons.

 NIK231: The 13C NMR spectrum reports 28 signals, but you would expect 26 signals.

Minor issues:

Ethyl acetate in two words

Line 91: CDCA do not triple, it reduces the concentration/dye loading.

OK

Reviewer 2 Report

The present manuscript by the Knyazeva group describes a synthesis of the novel titled compound 2 (NIK231) by using Suzuki-Miyaura cross-coupling and Knoevenagel condensation as two-step sequence.  The synthesis and the characterization of the new compounds seem sound and well-implemented.  The assay for the target compound showed suppressed aggregations and pai-pai stacking, and the addition of chenodeoxycholic acid (CDCD) provided the characteristic properties.    

However, the ¹H NMR and ¹³C NMR spectra of the novel compound 2 (NIK231) are not sufficiently pure.  The melting point was not described (amorphous?).  In the case that the property of compound 2 is not for suitable for these analyses, the methylated derivative of 2 will be acceptable for the reliable analysis using MeI/K₂CO₃ or TMSCHN₂.    

Thus, the reviewer recommends the publication in Molbank after revisions mentioned above and commented below.

<Comments & suggestions>

1.     Abstract; ¹H, ¹³C NMR, → ¹H and ¹³C NMRs,    Also, p. 2 line 53.

2.     P. 1, line 37; DSSC from it. → DSSC derived from “appropriate compound”.

3.     P. 1, line 43; gives → afforded

4.     P. 1, line 43; Condensation ... led to … → Knoevenagel condensation of aldehyde 2 with cyanoacetic acid led to …

5.     P. 2, line 50; unknown → novel

6.     P. 2, line 57; The sentence should be changed to “passive tense”.

7.     P. 2, line 57; pronounced → apparent

8.     P. 2, line 74; The structure of chenodeoxycholic acid (CDCD) should be illustrated in an additional Figure, due to smooth comprehension of readers.

9.     P. 2, line 77; is not so much → is moderate

10.  P. 4, lines 157 and 165; ethylacetate → ethyl acetate

11.  P. 4, line 174; On “purple solid” “mp” should be addressed.  Otherwise, the impossible reason for should be commented.