3-(Phenylethynyl)-7H-benzo[de]anthracen-7-one

Round 1

Reviewer 1 Report

The authors described the synthesis of 3-(phenylethynyl)-7H-benzo[de]anthracen-7-one. The photophysical properties were investigated by using UV-Vis and fluorescence spectroscopy in various organic solvents. Although the compound is reported in the Reaxys database, spectroscopic and analytical information is completely absent. ¹H and ¹³C NMR spectra show the presence of impurities. Thus, the formation of the compound is not conclusive. After purification of the compound, 1D and 2D NMR, IR, HRMS, and elemental analysis might be taken and included in both manuscript and Supplementary Material. Additional suggestions and comments are included: (1) The abstract might be re-structured. The most relevant data might be included. (2) See lines 56-64. The NMR and IR reporting data might be explained in a better form.   (3) See lines 56-64. The plausible mechanism might be included and briefly explained. (4) See Figure 1. It is necessary to improve the resolution. (5) See lines 71-77. The plausible mechanism responsible for the fluorescence phenome might be explained (ICT, among others). Moreover, the authors might explain why the quantum yield increases in ethanol. (6) See 3.2. Synthesis and Characterization. HRMS and IR data as well as elemental analysis might be included. The HRMS and IR spectra might be included in the Supplementary Material. In addition, the type of each carbon might be specified (i.e. CH or Cq); thus, APT or DEPT-135 might be taken and included in the Supplementary Material. (7) See Figure S2. It confirms that the compound has impurities. Did you perform UV-Vis measurements using a dirty compound? The ¹H NMR spectrum might be improved. (8) See Figure S4. It confirms that the compound has impurities. The ¹³C NMR spectrum might be improved. (9) See supplementary Material. HSQC, HMBC, COSY, HRMS, and IR spectra might be included. I recommend you purify it again. (10) See 2. Results and Discussion. In the end, a short conclusion might be included.

Author Response

Please see the attachment.

Author Response File: Author Response.pdf

Round 2

Reviewer 1 Report

The authors described the synthesis of 3-(phenylethynyl)-7H-benzo[de]anthracen-7-one. The photophysical properties were investigated by using UV-Vis and fluorescence spectroscopy in various organic solvents. Unfortunately, the authors performed very few changes, and most of them were exceedingly superficial. The rest of the modifications were not included by them. Surprisingly, the Supplementary Material was not included (¿are you sure that compound is clean? In this form, I cannot accept this manuscript.   (1) The abstract might be re-structured. The most relevant data might be included. (2) See lines 56-64. The NMR and IR reporting data might be explained in a better form.   (3) See lines 56-64. The plausible mechanism might be included and briefly explained. (4) See 3.2. Synthesis and Characterization. IR data as well as elemental analysis might be included. The HRMS and IR spectra might be included in the Supplementary Material. In addition, the type of each carbon might be specified (i.e. CH or Cq); thus, APT or DEPT-135 might be taken and included in the Supplementary Material. (5) See Figure S2. It confirms that the compound has impurities. ¿Did you perform UV-Vis measurements using a dirty compound? The ¹H NMR spectrum might be improved. (6) See Figure S4. It confirms that the compound has impurities. The ¹³C NMR spectrum might be improved. (7) See Supplementary Material. HSQC, HMBC, COSY, HRMS, and IR spectra might be included. I recommend you purify it again. (8) See 2. Results and Discussion. In the end, a short conclusion might be included.

Author Response

Please see the attachment.

Author Response File: Author Response.docx

Round 3

Reviewer 1 Report

The authors described the synthesis of 3-(phenylethynyl)-7H-benzo[de]anthracen-7-one. The photophysical properties were investigated by using UV-Vis and fluorescence spectroscopy in various organic solvents. The manuscript meets all requirements to be published in Molbank after minor revision. As mentioned in the previous revision, IR data and elemental analysis should be included. In particular, IR data are very important in this paper. Additional suggestions and comments are included: (1) See 3.2. Synthesis and Characterization. IR data as well as elemental analysis might be included as mentioned in the previous revision. In particular, IR reporting data and IR spectrum should be included in the manuscript and Supplementary Material, respectively.   (2) The ¹³C NMR reporting data shows 22 carbon signals, however, the compound has 23 carbon signals (12 CH and 11 Cq). It should be included in this form: ¹³C NMR (75 MHz, CDCl₃) δ 183.4 (C, C=O), 135.5 (C), 133.3 (CH), 133.3 (CH), 132.6 (C x 2), 131.8 (CH), 130.8 (C), 130.6 (CH), 130.1 (CH), 128.9 (CH), 128.6 (CH), 128.5 (CH), 128.1 (CH), 127.6 (CH), 127.1 (C), 126.9 (C), 123.4 (CH), 123.2 (C), 123.1 (CH), 122.9 (C), 97.0 (CºC), 87.1 (CºC). The APT spectrum allows the differentiation of CH and C signals. (3) See Figures S3 and S4. (a) APT spectrum instead of the ¹³C-NMR spectrum, and (b) CH₃ and CH signals appear with normal phase (up), while Cq and CH₂ signals appear with inverse phase (down). Thus, signals should be inverted by using the MestReNova program.   (4) See 2. Results and Discussion. In the end, a short conclusion might be included.

Author Response

Please see the attachment.

Author Response File: Author Response.pdf