BINUCLEAR GOLD(I) COMPOUNDS FOR PHOTOCATALYSIS APPLICATIONS

§103 §112

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 . In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status. Continued Examination Under 37 CFR 1.114 A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 28 August 2026 has been entered. New Examiner This application has been transferred to a new examiner, Nicholas Piro of Art Unit 1738, who can be reached at 571-272-6344. Information Disclosure Statements The Information Disclosure Statement filed on 5 December 2023 has been received and considered by the Examiner. Claim Rejections - 35 USC § 112 The following is a quotation of 35 U.S.C. 112(b): (b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention. The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph: The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention. Claims 2-3, 6-8, and 11-17 rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Claim 2 recites the limitation “(d) CY1-CY8 are independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted polyheteroaryl” as well as the limitation “with the proviso that when CY1-CY8 are independently substituted or unsubstituted aryl, R1-R8 are not substituted or unsubstituted alkyl.” This combination of limitations leaves it unclear what ligands are encompassed by the claim. In particular, all of the possible groups listed for CY1-CY8 in limitation (d) are aryl groups, whether they are further limited to polyaryl, heteroaryl, etc., or not. So, it would appear that R1-R8 can never be substituted or unsubstituted alkyl, yet substituted and unsubstituted alkyl are listed as possibilities for R1-R8 in (e). Furthermore, because CY1-CY8 may be substituted aryl groups (of various types), it is unclear what substituents are to be considered R1-R8 of the instant claim, and which are to be considered unidentified “substituents” on the aryls. For example, complex 5a may be considered as comprised of R1-R8 being alkyl groups (tBu) on polyaryl groups (terphenyl) that represent CY1-CY8, which would place the complex outside the limitations of claim 1, or it may be considered such that R1-R8 are 4-tert-butylphenyl (a substituted aryl) and CY1-CY8 are substituted phenyls. It is further unclear how “unsubstituted” aryls, polyaryls, heteropolyaryls, and polyheteroaryls, as listed in limitation (d), are covered by the claim, given that limitations (e) and (f) require these groups to be substituted with at least one non-hydrogen substituent. Claim 2 further recites “the substituents” in limitation (j). There is insufficient antecedent basis for this limitation in the claim. Claims 3, 6-8 and 11-17 depend upon claim 2 without resolving the indefiniteness and are likewise rejected. Regarding claim 12, several of the compounds illustrated in the claim appear to not meet the limitations of claim 2, and it is therefore indefinite whether these compounds are encompassed by the claim or not. For example, compound 2b contains a substituted alkyl group on an aryl CY1-CY8 and compound 5a contains an alkyl groups R1-R8 (tBu) on a polyaryl group (terphenyl), which falls within the broader classification of an aryl group. Furthermore, the lack of clarity in what constitutes CY1-CY8 as opposed to R1-R8 further means that under certain interpretations of claim 2, several more of the compounds recited in claim 12 would fail to meet all the limitations of the base claim (see below). Claim 6 recites the limitation "the substituents" in limitation (h). There is insufficient antecedent basis for this limitation in the claim. The following is a quotation of 35 U.S.C. 112(d): (d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers. The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph: Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers. Claim 12 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. At least compounds 2b and those pictured below fail to meet all the limitations of claim 2, as they contain substituted alkyl groups as R1-R8 on aryl phenyl groups CY1-CY8. PNG media_image1.png 246 272 media_image1.png Greyscale PNG media_image2.png 250 282 media_image2.png Greyscale Under a broader interpretation of “aryl” that encompasses heteroaryl and polyaryl groups, several more of the compounds also fail to meet the limitations of claim 2, including: PNG media_image3.png 234 520 media_image3.png Greyscale PNG media_image4.png 244 592 media_image4.png Greyscale It also appears at least the following additional compounds fail to meet the limitations of claim 2, as they lack any R1-R8 groups of the types listed in limitation (e) of claim 2: PNG media_image5.png 208 222 media_image5.png Greyscale PNG media_image6.png 192 232 media_image6.png Greyscale PNG media_image7.png 194 232 media_image7.png Greyscale It is noted that pending clarification of the limitations of claim 2, additional compounds within claim 12 may also fail to meet the limitations of claim 2. Applicant is asked to carefully consider whether each of the specific compounds recited in claim 12 meet all the limitations of the amended independent claim. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements. Claim Rejections - 35 USC § 103 The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action: A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made. The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows: 1. Determining the scope and contents of the prior art. 2. Ascertaining the differences between the prior art and the claims at issue. 3. Resolving the level of ordinary skill in the pertinent art. 4. Considering objective evidence present in the application indicating obviousness or nonobviousness. This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention. Claims 2-3, 6-8 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Ikeda et al. (JP 2008074905 A; Document #3 on the IDS filed 5 December 2023). The provided English machine translation of Ikeda (JP 2008074905 A) is referenced in the analysis below. Regarding claim 2, Ikeda teaches gold complexes of the general formula PNG media_image8.png 156 200 media_image8.png Greyscale ([0004] of translation and p. 2 of original), as well as the following more specific complexes (p. 11 of original): PNG media_image9.png 438 846 media_image9.png Greyscale . Though none of these complexes pictured in the examples of Ikeda meet the limitations of claim 2, Ikeda further teaches that the aryl groups on the phosphines (R1 to R10) may instead be 2-, 3-, or 4-biphenyl ([0013]), which meets the limitations of the instant claim by CY1-CY8 being phenyl and R1-R8 of the instant claim being phenyl, an unsubstituted aryl, where n1-n8 are 1, Z1 and Z2 are chloride, and L1 is CH2. The structure of this compound is pictured below. PNG media_image10.png 200 400 media_image10.png Greyscale Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute the aryl groups in the diphosphinogold(I) chloride dimers of Ikeda with biphenyl groups, as taught by Ikeda, thereby arriving at the instantly claimed invention. One of ordinary skill in the art would have been motivated to do so because Ikeda teaches that these alternate substituents are specific examples of acceptable R groups in their complexes. Regarding claim 3, Ikeda teaches the complex of claim 2, where the complex pictured above meets the limitations of claim 3 with L1 and L2 being CH2, i.e., R9 and R10 as identified in the instant claim are each hydrogen and n9 is one. Regarding claims 6 and 7, Ikeda teaches the complex of claim 2, where the complex pictured above meets the limitations of Formula IIa with n10 and n12 being 1, R1-R8 being phenyl (an unsubstituted aryl), n1-n8 being 1, and Z1 and Z2 being chloride. Regarding claim 8, Ikeda teaches the complex of claim 2, where the complex pictured above has R1-R8 being phenyl, i.e. R14 is hydrogen and n14 is 5. Regarding claim 11, Ikeda teaches the complex of claim 2 where there are no occurrences of A’, and therefore claim 11 imposes no further limitations on the structure picture above, which also satisfies the limitations of the instant claim. Claims 2-3, 6-8, and 11-17 are rejected under 35 U.S.C. 103 as being unpatentable over Bayrakdar et al. (Chem Soc. Rev. 2020, 49(19), 7044-7100, DOI: 10.1039/d0cs00438c; Document #5 on the IDS filed 5 December 2023) in view of Ikeda et al. (JP 2008074905 A; Document #3 on the IDS filed 5 December 2023). Regarding claims 2-3, 6-8, and 11, Bayrakdar teaches the [Au2(dppm)2](ClO4)2 complex (Scheme 74), and further teaches that compounds with the [Au2(dppm)2]2+ cation make good photoredox catalysts in their excited states because of their long lifetimes and them being powerful reductants in their excited state (p. 7071, col. 2). Bayrakdar does not teach any structure meeting the limitations of claim 2. However, Ikeda also teaches a series of dinuclear gold complexes that like Au2(dppm)2Cl2 may serve in phosphorescent devices emitting blue light ([0008]), suggesting that they too have highly reducing, long-lived excited states. In particular, Ikeda teaches gold complexes of the following general formula PNG media_image8.png 156 200 media_image8.png Greyscale ([0004] of translation and p. 2 of original), as well as the following more specific complexes (p. 11 of original): PNG media_image9.png 438 846 media_image9.png Greyscale . Though none of the complexes pictured in the examples of Ikeda meet the limitations of claim 2, Ikeda further teaches that the aryl groups on the phosphines, Ikeda’s R1 to R10, may instead be 4-biphenyl, or 3,5-diphenylphenyl, among other choices ([0013]). Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute the phenyl groups of dppm in [Au2(dppm)2](ClO4)2 for 4-biphenyl or 3,5-diphenylphenyl, as taught by Ikeda, thereby arriving at complexes PNG media_image11.png 160 400 media_image11.png Greyscale and PNG media_image12.png 131 400 media_image12.png Greyscale , which each meet the limitations of claims 2-3, 6-8 and 11. One of ordinary skill in the art would have been motivated to replace the phenyl groups in the complexes of Bayrakdar with 4-biphenyl or 3,5-diphenylphenyl groups because Ikeda teaches that such substitution is likely to have similar photochemical properties, and one of ordinary skill would therefore expect them to be similarly effective photocatalysts to the unsubstituted species taught by Bayrakdar. Regarding claim 12, Bayrakdar teaches the [Au2(dppm)2](ClO4)2 complex (Scheme 74), and further teaches that compounds with the [Au2(dppm)2]2+ cation make good photoredox catalysts in their excited states because of their long lifetimes and them being powerful reductants in their excited state (p. 7071, col. 2). Bayrakdar does not teach any of the substituted dppm ligands required by the instant claim. However, Ikeda also teaches a series of dinuclear gold complexes that like Au2(dppm)2Cl2 may serve in phosphorescent devices emitting blue light, suggesting that they too have highly reducing, long-lived excited states. Ikeda teaches gold complexes of the following general formula, PNG media_image8.png 156 200 media_image8.png Greyscale ([0004] of translation and p. 2 of original), as well as the following more specific complexes (p. 11 of original): PNG media_image9.png 438 846 media_image9.png Greyscale Though none of the complexes pictured in the examples of Ikeda meet the limitations of claim 2, Ikeda further teaches that the aryl groups on the phosphines (R1 to R10) may instead be 9-anthryl ([0013]). Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute the phenyl groups of dppm in [Au2(dppm)2](ClO4)2 for 9-anthryl groups, as taught by Ikeda, thereby arriving at the complex PNG media_image5.png 208 222 media_image5.png Greyscale , which is one of those recited in claim 12. One of ordinary skill in the art would have been motivated to replace the phenyl groups with 9-anthryl groups because Ikeda teaches that such a complex is likely to have similar photochemical properties, and one of ordinary skill would therefore expect it to be a similarly effective photocatalyst to the unsubstituted version taught by Bayrakdar. Regarding claims 13-17, modified Bayrakdar teaches gold complexes meeting the limitations of claim 2, including PNG media_image11.png 160 400 media_image11.png Greyscale and PNG media_image12.png 131 400 media_image12.png Greyscale , as analyzed above. The 3,5-diphenylphenyl complex is expected to be electronically similar to complex 5a of the instant disclosure, differing only by the absence of tBu groups distant from the metal. Therefore, this complex would be expected to have similar photophysical properties to those of complex 5a. The biphenyl complex is also expected to have properties similar to complex 5a while also falling between complexes 2b and 3b, which are more electron-deficient and more electron-rich, respectively, due to the presence of CF3 and OMe groups. Therefore, it is concluded that at least the biphenyl and 3,5-diphenylphenyl complexes suggested by Bayrakdar and Ikeda will also have absorption profiles, extinction coefficients, radiative decay rates, quenching rate constants, and reduction potentials that fall in the instantly claimed ranges. Once a reference teaching product appearing to be substantially identical is made the basis of a rejection, and the examiner presents evidence or reasoning to show inherency, the burden of proof shifts to the applicant. “[T]he PTO can require an applicant to prove that the prior art products do not necessarily or inherently possess the characteristics of [their] claimed product. Whether the rejection is based on inherency’ under 35 U.S.C. 102, on prima facie obviousness’ under 35 U.S.C. 103, jointly or alternatively, the burden of proof is the same, and its fairness is evidenced by the PTO’s inability to manufacture products or to obtain and compare prior art products.” In re Best, 562 F.2d 1252, 1255, 195 USPQ 4380, 483-34 (CCPA 1977)), see MPEP 2112. Applicant has not clearly shown an unobvious difference between the instant invention and the prior art’s product. Pertinent Prior Art The following prior art made of record and not relied upon is considered pertinent to applicant's disclosure: Mirabelli et al. (Journal of Medicinal Chemistry 1987, 30(12), 2181-2190) disclose amino-substituted aryl diphosphine ligands for gold complexes. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to Nicholas A Piro whose telephone number is (571)272-6344. The examiner can normally be reached Mon-Fri, 8:00 am-5:00 pm. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sally Merkling can be reached at (571) 272-6297. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /NICHOLAS A. PIRO/Assistant Examiner, Art Unit 1738 /PAUL A WARTALOWICZ/Primary Examiner, Art Unit 1735