4,7-Di(9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine
Round 1
Reviewer 1 Report
In this contribution Rakitin and coworkers designed the titled compound (4,7-Di(9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine) by aromatization of the 1,2,3,4,4a,9a-hexa- 11 hydro-9H-carbazol-9-yl precursor. Originality of this short note is limited taking into account the 1,2,5]thiadiazolo[3,4-d]pyridazine analogue was described recently by the same team. Nevertheless the title compound is new and fits therefore the scope of the journal. I therefore recommend the publication of this short note after adressing the folowing points:
1- I clearly do not agree with the 1st sentence of abstract: efficient active layer in NIR-OLEDs are essentiannly base don transition metal complexes. Traditional fluorescent emitters are not anymore interesting for OLED applications (only singlet excitons (25%) and be used with such emitters. TADF chromophores are interesting for blue (or eventually green-yellow) emission.
2- l 15: The sentence is not gramatically correct: I would suggest the photophysical properties of the title compound were...
3- the sentence l32-33 is confusing: the Molbank short note (ref 16) clearly do not describe any effective OLED application of precursor 1.
4- l 58-60: It is presouptious to attribute the nature of the absortion band only beause to solvatochromism is observed (same is observed for n-pi* transition).
5- l 61-63: according to the data is ESI this is only in chloroform that a red-shift of the ICT band is observed. Talking red shift of the band with increasing polazrity is not correct here.
6- I would suggest to put all photophysical data in the main text 5Table S1) and to discuss them a bit more. It would have been interesting to measure emission quantum yield (comparative method does not required other aparatus than those used for registering the spectra). If possible lifetime measurement would be interesting. What about solid state emission?
7- l 69-73: As explained in point 1: we NIR-OLED application is far, and in any case the term "phosphor" is not adapted.
8- In 1H nmr descrition, please provide unit for coupling constant. For the signals at 7.53 and 7.47 the relative integration is wrong (it should be 4 H)
9- It is not reasonable to provide molar absorption coefficent with so many significant digits: I suspect that the mass weighted for solution preparation is known with no more than 3 significant digits in the best case.
10- Ref 1: the journal name abbreviation is Dyes Pigm.
11- Fif S6: It would be better to plot molar absorption coefficient vs wavelength (best option) Another alternative would be to add concentration in the caption or to normalized the spectra.
12- Figure S7: the concentration (if the same for all compounds) should be specified in the caption. Otherwise the spectra should be normalized.
13- Stokes shifts in Tables S1 should be expressed as wavenumber difference (in cm-1), proportional to energy.
Author Response
Professor Oleg A. Rakitin
FRSC
Head of the Laboratory
N.D. Zelinsky Institute of Organic Chemistry RAS
Leninsky Prospekt, 47, Moscow, 119991 Russia
tel. 7-499-1355327
fax 7-499-1355328
e-mail: orakitin@ioc.ac.ru
Dear Editor,
Thank you very much for your positive reply on our manuscript (Manuscript ID: molbank-1859418). We also greatly appreciate the reviewer for his kind comments and suggestions. We have carefully checked the manuscript again, and revised it as proposed (all revisions made to the manuscript were marked up using the “Track Changes” function).
We hope that such modification and reply can meet your and reviewer’s requirement. Thank you very much for your consideration!
Sincerely yours,
Oleg Rakitin
Reviewer 1
The authors are grateful to the reviewer for a kind and highly professional review.
Point 1.
I clearly do not agree with the 1st sentence of abstract: efficient active layer in NIR-OLEDs are essentiannly base don transition metal complexes. Traditional fluorescent emitters are not anymore interesting for OLED applications (only singlet excitons (25%) and be used with such emitters. TADF chromophores are interesting for blue (or eventually green-yellow) emission.
Response from authors.
Corrected as suggested by the reviewer.
Point 2.
l 15: The sentence is not gramatically correct: I would suggest the photophysical properties of the title compound were...
Response from authors.
Corrected as suggested by the reviewer.
Point 3.
the sentence l32-33 is confusing: the Molbank short note (ref 16) clearly do not describe any effective OLED application of precursor 1.
Response from authors.
Corrected as suggested by the reviewer.
Point 4.
l 58-60: It is presouptious to attribute the nature of the absortion band only beause to solvatochromism is observed (same is observed for n-pi* transition).
Response from authors.
Corrected as suggested by the reviewer.
Point 5.
l 61-63: according to the data is ESI this is only in chloroform that a red-shift of the ICT band is observed. Talking red shift of the band with increasing polazrity is not correct here.
Response from authors.
Corrected as suggested by the reviewer.
Point 6.
I would suggest to put all photophysical data in the main text 5Table S1) and to discuss them a bit more. It would have been interesting to measure emission quantum yield (comparative method does not required other aparatus than those used for registering the spectra). If possible lifetime measurement would be interesting. What about solid state emission?
Response from authors.
The table has been moved to the article. The text of the table is supplemented. The quantum yield of luminescence could not be measured by the relative method, due to the extremely low luminescence intensity. Luminescence in the solid state was not measured.
Point 7.
l 69-73: As explained in point 1: we NIR-OLED application is far, and in any case the term "phosphor" is not adapted.
Response from authors.
Corrected as suggested by the reviewer.
Point 8.
In 1H nmr descrition, please provide unit for coupling constant. For the signals at 7.53 and 7.47 the relative integration is wrong (it should be 4 H)
Response from authors.
Corrected as suggested by the reviewer.
Point 9.
It is not reasonable to provide molar absorption coefficent with so many significant digits: I suspect that the mass weighted for solution preparation is known with no more than 3 significant digits in the best case.
Response from authors.
Corrected as suggested by the reviewer.
Point 10.
Ref 1: the journal name abbreviation is Dyes Pigm.
Response from authors.
Corrected as suggested by the reviewer.
Point 11.
Fif S6: It would be better to plot molar absorption coefficient vs wavelength (best option) Another alternative would be to add concentration in the caption or to normalized the spectra.
Response from authors.
Сoncentrations are added to the title.
Point 12.
Figure S7: the concentration (if the same for all compounds) should be specified in the caption. Otherwise the spectra should be normalized.
Response from authors.
Сoncentrations are added to the title.
Point 13.
Stokes shifts in Tables S1 should be expressed as wavenumber difference (in cm-1), proportional to energy.
Response from authors.
Corrected as suggested by the reviewer.
Round 2
Reviewer 1 Report
There are still correction required before publication. Autohrs should take more care in their correction
l 15: The photophysical properties....
l 56-57: several spectral bands in the UV range of wavelengths attributed to π-π* transition.
l66 The large Stokes shifts of 4700 and 4790 cm-1
l77 for 4,7-di... (missing space)
Table1: Absorption/emission maxima should be only provided as wavelength in nm. Stokes shifts should be only provided as wavenumber difference with no more than 3 significant digits (remove the data in nm)
in experimental part the UV vis and emission data could be removed (they are already provided in Table 1) and in any case the number of significant digits for molar absorption coefficient should be amended.
Journal name of ref 18 is not corectly abbreviated.
Author Response
Reviewer 1
There are still correction required before publication. Autohrs should take more care in their correction
l 15: The photophysical properties....
l 56-57: several spectral bands in the UV range of wavelengths attributed to π-π* transition.
l66 The large Stokes shifts of 4700 and 4790 cm-1
l77 for 4,7-di... (missing space)
Table1: Absorption/emission maxima should be only provided as wavelength in nm. Stokes shifts should be only provided as wavenumber difference with no more than 3 significant digits (remove the data in nm)
in experimental part the UV vis and emission data could be removed (they are already provided in Table 1) and in any case the number of significant digits for molar absorption coefficient should be amended.
Journal name of ref 18 is not corectly abbreviated.
Response from authors.
All comments are taken into account and corrected as suggested by the reviewer.
