DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-15 in the reply filed on 08/24/2025 is acknowledged.
Response to Amendment
The amendment filed on 08/24/2025 has been entered into the prosecution of the application.
Currently, claim(s) 1-8 and 10-15 is/are pending examination.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim(s) 1-3, 6-7, 10-12, and 14-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ruiz Espelt, Laura, et al. "Enantioselective conjugate additions of α-amino radicals via cooperative photoredox and Lewis acid catalysis." Journal of the American Chemical Society 137.7 (2015): 2452-2455 (hereinafter referred to as Espelt) in view of Shi (Adv. Synth. Catal. 2020, 362, 2143– 2149).
As to claim 1, Espelt pertain to the instant invention because Espelt relates to forming a carbon-carbon (C-C) through a C-H bond activation using a visible light (Espelt, Table 1).
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Table 1 of Espelt
Espelt teaches to “irradiating the mixture at a suitable wavelength to form photo-catalytically a carbon-carbon (C-C) bond between a sp3 carbon atom having an activated carbon-hydrogen bond alpha to the nitrogen atom of the alkylamine sp2carbon atom beta to the alpha, beta-unsaturated carbonyl” (Espelt, Table 1).
Espelt does not explicitly teach “contacting a lead halide perovskite, redox substrates comprising an alkylamine and alpha, beta-unsaturated carbonyl, and solvent to form a mixture.”
Shi pertains to the instant invention because Shi relates to a photo-catalytic synthesis of an organic molecule (Shi, abstract).
Shi teaches to “contacting a lead halide perovskite, first redox substrate, second redox substrate, and solvent to form a mixture (CsPbBr3 is acting as a photocatalyst for the mixture; Shi, Table 1). Shi discloses irradiating the mixture at a suitable wavelength to form at least one covalent bond between the first redox substrate and second redox substrate (using substrates 1a and 2a dissolved in solvent in presence of air under LEDs for direct aminomethylation; Shi, Table 1). Shi discloses that the perovskite photo-catalyzes formation of a C-C bond via C-H activation (Shi, pg. 2144).
Both Espelt and Shi relate to forming a carbon-carbon (C-C) through a C-H bond activation using a visible light (Espelt, Table 1; Shi, pg. 2144). Espelt does not explicitly teach using a lead halide perovskite as a photoredox catalysts. Espelt does teach using Ru(bpy)3Cl2 as a photoredox catalyst (Espelt, Table 1). Shi teaches a lead halide perovskite (CsPbBr3 is acting as a photocatalyst for the mixture; Shi, Table 1). Shi discloses irradiating the mixture at a suitable wavelength to form at least one covalent bond between the first redox substrate and second redox substrate (using substrates 1a and 2a dissolved in solvent in presence of air under LEDs for direct aminomethylation; Shi, Table 1). Shi discloses that the perovskite photo-catalyzes formation of a C-C bond via C-H activation (Shi, pg. 2144).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have modified the photocatalyzed formation of C-C bond via C-H activation of Espelt with the lead halide perovskite of Shi for enabling photocatalyzed formation of C-C bond via C-H activation.
In regards to claim 2, Espelt in view of Shi discloses an alkali metal, Cs (Shi, Scheme 1).
In regards to claim 3, Espelt in view of Shi discloses CsPbBr3 (Shi, Scheme 1).
As to claim 6, Espelt in view of Shi teaches “wherein the perovskite is in the form of a nanocrystal or colloid” (TEM images showed that the sizes of CSPbBr3 catalyst becomes smaller with no significant change in the shape; Shi, pg. 2147, Fig. S6 in the supporting information of Shi).
As to claim 7, Espelt in view of Shi teaches “wherein the perovskite has an average particle size of about 1 nanometer to about 150 nanometers” (TEM images showed that the sizes of CSPbBr3 catalyst becomes smaller with no significant change in the shape; Shi, pg. 2147, Fig. S6 in the supporting information of Shi, wherein Figure S6 shows that a dimension of the particle sizes are at least smaller than 100 nm after 5th reaction).
In regards to claim 10, Espelt in view of Shi discloses irradiating CsPbBr3 with white, red, green, or blue LEDs (Shi, Table 1).
In regards to claim 11, Espelt in view of Shi discloses irradiating CsPbBr3 with white, red, green, or blue LEDs (Shi, Table 1). One of ordinary skill in the art would have utilized wavelengths that read into the claimed range (355 nm to 465 nm).
In regards to claim 12, Espelt in view of Shi discloses using CH2Cl2 (Shi, Table 1).
In regards to claim 14, Espelt in view of Shi discloses that the mixture is contacting oxygen that exists in air (Shi, Table 1).
As to claim 15, Espelt in view of Shi teaches to the method of claim 14, wherein the mixture is contacting an acidic additive (Lewis acid catalyst, scandium triflate, is added together; Espelt, Table 1).
Claim(s) 4-5 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ruiz Espelt, Laura, et al. "Enantioselective conjugate additions of α-amino radicals via cooperative photoredox and Lewis acid catalysis." Journal of the American Chemical Society 137.7 (2015): 2452-2455 (hereinafter referred to as Espelt) in view of Shi (Adv. Synth. Catal. 2020, 362, 2143– 2149), as applied to claim 1 above, and in further view of Zhang (Org. Lett. 2010, 12, 21, 4745–4747), and in further view of Creutz (Chem. Mater. 2018, 30, 4887−4891).
In regards to claim 4, Espelt in view of Shi does not disclose a pretreatment of the photocatalyst with a trialkylsilylhalide.
Creutz pertains to Espelt in view of Shi because Creutz relates to lead halide perovskite (Creutz, Scheme 1). Creutz discloses using trimethylsilyl halides in pretreating perovskites (Creutz, page 4887, third paragraph).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the instant invention to combine the method of Espelt in view of Shi and the trimethylsilyl halides of Zhang for pretreatment. One could have combined the disclosed ideas, and results of the combination would have been predictable because all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results to one of ordinary skill in the art.
In regards to claim 5, Espelt in view of Shi does not disclose CsPbBr3-yXy, wherein X is Cl or I, and y is 1-3.
Creutz discloses that treatment of CsPbBr3 with TMSI, generating CsPbBr3xI3(1−x) nanocrystals (Creutz, Fig. 1).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the instant invention to combine the method of Espelt in view of Shi and the trimethylsilyl halides of Creutz for pretreatment. One could have combined the disclosed ideas, and results of the combination would have been predictable because all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results to one of ordinary skill in the art.
Claim(s) 8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ruiz Espelt, Laura, et al. "Enantioselective conjugate additions of α-amino radicals via cooperative photoredox and Lewis acid catalysis." Journal of the American Chemical Society 137.7 (2015): 2452-2455 (hereinafter referred to as Espelt) in view of Shi (Adv. Synth. Catal. 2020, 362, 2143– 2149), as applied to claim 1 above, and in further view of Noble, Adam, and David WC MacMillan. "Photoredox α-vinylation of α-amino acids and N-aryl amines." Journal of the American Chemical Society 136.33 (2014): 11602-11605 (hereinafter referred to as Noble).
As to claim 8, Espelt in view of Shi does not explicitly teach “wherein the alkylamine is an N-aryl substituted nitrogen heterocycloalkyl”.
Noble pertains to the instant invention because Noble relates to C-C bond formation via C-H activation with a photocatalyst (Noble, Table 1).
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Table 1 of Noble
Noble teaches “wherein the alkylamine is an N-aryl substituted nitrogen heterocycloalkyl” (Noble, Table 1).
Both Espelt in view of Shi and Noble relate to C-C bond formation via C-H activation with a photocatalyst (Noble, Table 1). Espelt in view of Shi does not explicitly teach an N-aryl substituted nitrogen heterocycloalkyl as an alkylamine. Noble does teach an N-aryl substituted nitrogen heterocycloalkyl as an alkylamine.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have modified the method of Espelt in view of Shi with the redox substrate of Noble for enabling photocatalyzed formation of C-C bond via C-H activation.
Response to Arguments
Applicant’s arguments, see page 6 of 10, filed 02/21/2025, with respect to the rejection(s) of claim(s) 1 under 35 U.S.C. 103 have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of Shi (Adv. Synth. Catal. 2020, 362, 2143– 2149) in view of Ruiz Espelt, Laura, et al. "Enantioselective conjugate additions of α-amino radicals via cooperative photoredox and Lewis acid catalysis." Journal of the American Chemical Society 137.7 (2015): 2452-2455 (hereinafter referred to as Espelt).
In particular, the declaration filed 02/21/2025 under 37 CFR 1.130 has been received. As a result, Zhu reference is deemed to be within the exception provided by 35 U.S.C. 102(b)(1)(A) and therefore not citable as prior art. However, Shi remains as a prior art because the inventor is not a common inventor of Shi and therefore fails to provide that the applicant owned Shi.
Please refer to the rejection above.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Huang, Haowei, et al. "C (sp3)–H bond activation by perovskite solar photocatalyst cell." ACS Energy Letters 4.1 (2018): 203-208 (hereinafter referred to as Huang) teaches that perovskite enable C-H activation. Wan, Qiang, et al. "Perovskite-supported Pt single atoms for methane activation." Journal of Materials Chemistry A 8.8 (2020): 4362-4368 (hereinafter referred to as Wan) teaches that perovskites enable C-H activation.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/JOHN LEE/Examiner, Art Unit 1794
/JAMES LIN/Supervisory Patent Examiner, Art Unit 1794