WATER-SOLUBLE TETRAHYDROPYRENE BASED FLUORESCENT POLYMERS

§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 . Election/Restrictions Claims 13-15 withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on September 15, 2026. Applicant’s election without traverse of claims 1-12 and 16 in the reply filed on September 15, 2026 is acknowledged. The examiner agrees with the applicants reply filed to the original Restriction Requirement given Easwaran (WO2017180998A2) did not specifically disclose “at least one A” selected from the claimed group of tetrahydropyrenes (THP). The examiner apologizes for the oversight in the original restriction requirement. However, as cited in the rejection of claim 1 below, the technical feature as recited is rendered obvious in the art and thus the restriction requirement is maintained. The examiner reminds the applicant of the potential of rejoinder of withdrawn claims if the linking technical feature is found to be allowable over the art. Specification The lengthy specification has not been checked to the extent necessary to determine the presence of all possible minor errors. Applicant’s cooperation is requested in correcting any errors of which applicant may become aware in the specification. 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 1-12 and 16 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 1 recites identities of R1 and R2 wherein both include: PNG media_image1.png 93 117 media_image1.png Greyscale . However, the R7 group is not defined as currently presented. Thus, claim 1 is indefinite as it is unclear as to what satisfies the R7 group. Considering the other substituents claimed, R7 is likely R3 or R4 and thus will be interpreted as such. Claims 2-12 and 16 are rejected as being dependent on, and failing to cure the deficiencies of, rejected independent claim 1. Claim 4 presents three sets of formulas: VIa-b, VIIa-b, and VIIIa-b. However, the individual pairings do not appear to have patentable weight from each other. The formulas between each pairing appear to be identical, thus it is unclear as to what distinguishes between VIa and VIB, VIIa, and VIIb, and VIIIa and VIIIb. VIa and VIb are provided for reference: PNG media_image2.png 426 346 media_image2.png Greyscale . The formulas appear identical. Claim 5 recites limitations of formulaic structures for a water-soluble fluorescent copolymer wherein structures for “A” have subscripts “g”. The subscript “g” is undefined as claimed, thus it is unclear to what amount “g” can be included in such formulae to satisfy the invention as claimed. Thus, claim 5 is indefinite. For the purposes of examination, the subscript “g” will be interpreted as subscript “a” considering the co-polymeric block is assumed under unit “A” as claimed. 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. Claims 1-12 are rejected under 35 U.S.C. 103 as being unpatentable over Easwaran et al (WO201780998A2, hereinafter Easwaran Doc#1) in view of Kawano et al (US PGPub 20140357898) and Easwaran et al (US PGPub 20200190253, hereinafter Easwaran Doc#2) as evidenced by El-Ballouli et al (NPL: “Diarylpyrenes vs diaryltetrahydropyrenes…”). Regarding claim 1, Easwaran et al (Doc#1) teach a water soluble fluorescent polymer which is encompassed by the shared technical feature of the instant application. Easwaran teaches the following structure (see paragraph [0008] spanning pgs 2-5: PNG media_image3.png 217 531 media_image3.png Greyscale wherein the first compound (dihydrophenanthrene DHP unit) is a potential “A” group as claimed (aryl or heteroaryl) except does not include the limitation “wherein at least one A is selected from the group consisting of…”, the double bond is identical as claimed, the “M” group is identical as claimed, and the “L” group is identical as claimed. Easwaran et al do not encompass an additional “M’” group that is optionally included. Further, “a”, “b”, “c”, “d”, and “m” are identical to as claimed. Pgs 2-10 of Doc#1 further define G1, G2, M, L, R1, R2, X, and Y which are identical or strongly overlap to the disclosed identities of those claimed as well. Substituting portions of the aryl unit with R, X, and Y groups as disclosed along with inclusion of disclosed linker L molecules enables energy transfer for acceptor based dyes in fluorescence based applications: PNG media_image4.png 274 492 media_image4.png Greyscale (pg 23 of Doc#1). Doc#1 does not disclose “A” such that a tetrahydropyrene (THP) molecule or unit is included which are the molecules recited in claim 1: PNG media_image5.png 158 634 media_image5.png Greyscale . Kawano teaches fluorescent polymers which include substituted THP monomer units flanked by optional aryl units (paragraph [0008]) PNG media_image6.png 275 272 media_image6.png Greyscale . R5 and R6 substituents can be optionally included as disclosed by Kawano, along with the flanking aryl units considering m, n1, and n2 can all be 0 as shown in formula Ia (paragraph [0025]): PNG media_image7.png 274 270 media_image7.png Greyscale which serve to improve solubility and improve film-forming properties. Kawano does not disclose that such THP groups are fluorescent. El-Ballouli characterizes such groups in their embodiments and teaches they can be strongly fluorescent and utilized in such applications (Scheme 1 and Fig. 5). Easwaran in Doc#2 teaches, similarly to Kawano, that aryl/aromatic monomeric units can be combined together for a fluorescent polymer which is water-soluble, analogous to the embodiment of Easwaran Doc#1 (paragraph [0084]): PNG media_image8.png 558 272 media_image8.png Greyscale . Additionally, the “B” group of Doc#2 satisfies the optionally included M’ as claimed considering B is randomly or “non-randomly” (reads on “evenly”) distributed and modifies the polymer through adjusting the bandgap (paragraph [0090]). It would have been prima facie obvious to one of ordinary skill in the art, as of the effective filing date, to include a “B” group distributed along the polymer in Doc#1 in order to modify the bandgap of the polymer and arrive at the optional limitation as claimed. Thus, in Doc#2, Easwaran teaches combination of Kawano’s THP-based unit into a multi-aryl polymer which can be applied into the aryl/heteroaryl dihydrophenanthrene polymer of Easwaran in Doc#1. It would have been prima facie obvious to one of ordinary skill in the art, as of the effective filing date, to further provide another fluorescent aryl group such as the THP monomer of Kawano into the DHP-based water-soluble fluorescent polymer of Easwaran (Doc#1), as informed by Easwaran (Doc#2), and substitute at known substitution positions disclosed in Doc#1 with known X, Y, R1, and R2 of Doc#1 as known suitable substituents capable of imparting water-solubility and maintaining fluorescence and as a known combination of fluorescent aryl groups for use in conjugated water soluble fluorescent polymers and arrive at the invention as claimed. Thus, Easwaran and Kawano teach the claimed “ PNG media_image9.png 645 691 media_image9.png Greyscale PNG media_image10.png 802 633 media_image10.png Greyscale PNG media_image11.png 762 614 media_image11.png Greyscale PNG media_image12.png 200 613 media_image12.png Greyscale ” Regarding claim 2, Easwaran and Kawano teach the water-soluble fluorescent polymer of claim 1. As described in the rejection of claim 1 above, Kawano teaches a THP molecule for use in polymers (fluorescent monomer as evidenced by El-Ballouli and thus fluorescent polymers of Easwaran). Kawano further teaches the molecule can include substituents at the X and Y positions as claimed and thus analogous to Easwaran locations in the top/middle ring of DHP molecules. Easwaran in Doc#2 teaches combination of aryl monomers in such polymers of Doc#1. Easwaran in both docs teaches suitable R1 and R2 type groups that overlap and/or are identical with those as claimed. In Doc#1, Easwaran teaches the matching substituent(s) of claimed formulas IIa-c, IIIa-c, and IVa-c: PNG media_image13.png 565 507 media_image13.png Greyscale PNG media_image14.png 372 500 media_image14.png Greyscale . In Doc#2, the substituent of formulas Ia-c are disclosed (paragraphs [0004-20]): PNG media_image15.png 245 266 media_image15.png Greyscale PNG media_image16.png 324 267 media_image16.png Greyscale wherein W, the Ls, and E overlap with the W, Ls, and R4 as claimed, respectively. It would have been prima facie obvious to one of ordinary skill in the art, as of the effective filing date, to select for any of the substituting groups as disclosed by Easwaran in either document as known substituents proper for water soluble polymers when combined with the THP monomers of Kawano and arrive at the invention as claimed. Thus, Easwaran and Kawano teach the claimed “ PNG media_image17.png 457 598 media_image17.png Greyscale PNG media_image18.png 683 408 media_image18.png Greyscale PNG media_image19.png 721 366 media_image19.png Greyscale PNG media_image20.png 744 354 media_image20.png Greyscale PNG media_image21.png 410 350 media_image21.png Greyscale ”. Regarding claim 3, Easwaran and Kawano teach the water-soluble fluorescent polymer of claim 1. In Doc#1, Easwaran teaches the molecule as claimed for DHP which, when substituted for THP group substituted identically of Kawano, matches the formulas as claimed for Va-Vc: PNG media_image22.png 189 465 media_image22.png Greyscale . It would have been prima facie obvious to one of ordinary skill in the art, as of the effective filing date, to swap the DHP molecule of Easwaran, while maintaining the top substituents and optionally substituting the bottom ring, for a THP molecule of Kawano or further include the THP molecule, as informed by Easwaran in Doc#2, as a known alternative fluorescent molecule capable of use in fluorescent water soluble polymers and arrive at the invention as claimed. Thus, Easwaran and Kawano teach the claimed “ PNG media_image23.png 272 586 media_image23.png Greyscale PNG media_image24.png 522 256 media_image24.png Greyscale ”. Regarding claim 4, Easwaran and Kawano teach the water-soluble fluorescent polymer of claim 1. Easwaran in Doc#1 teaches the substituents matching those of formulas VI, VII, and VIII: PNG media_image25.png 454 480 media_image25.png Greyscale PNG media_image26.png 187 439 media_image26.png Greyscale . Although Easwaran does not teach substituting a THP molecule, Kawano teaches THP can be substituted on the bottom middle ring at the same locations of X and Y as claimed. It would have been prima facie obvious to one of ordinary skill in the art, as of the effective filing date, to include the THP monomer of Kawano as a known suitable fluorescent monomer for use in fluorescent polymers and substitute with any of the overlapping substitutents as known suitable substitutents for water soluble fluorescent polymers and further substitute on the lower ring as a known suitable substitution site for such monomers and arrive at the invention as claimed. Thus, Easwaran and Kawano teach the claimed “ PNG media_image27.png 80 587 media_image27.png Greyscale PNG media_image28.png 683 337 media_image28.png Greyscale PNG media_image29.png 533 354 media_image29.png Greyscale PNG media_image30.png 260 327 media_image30.png Greyscale ”. Regarding claim 5, Easwaran and Kawano teach the water-soluble fluorescent polymer of claim 1. Easwaran Doc#1 teaches the substituents of formulas XIV-XVII: PNG media_image25.png 454 480 media_image25.png Greyscale PNG media_image26.png 187 439 media_image26.png Greyscale wherein Z can be “O” (line 5 pg 3) and Q can be NH (lines 6-7, pg3). Easwaran Doc#1 also teaches the additional heteroaryl group with the 5-membered ring: PNG media_image31.png 228 475 media_image31.png Greyscale PNG media_image32.png 285 487 media_image32.png Greyscale wherein X has the same identity as previously disclosed (independently selected from the group consisting of a C and Si). It would have been prima facie obvious to one of ordinary skill in the art, as of the effective filing date, to include the THP monomer of Kawano as a known suitable fluorescent monomer for use in fluorescent polymers and substitute with any of the overlapping substituents as known suitable substituents for water soluble fluorescent polymers and further substitute on the lower ring as a known suitable substitution site for such monomers and arrive at the invention as claimed. Thus Easwaran and Kawano teach the claimed “ PNG media_image33.png 398 590 media_image33.png Greyscale PNG media_image34.png 645 428 media_image34.png Greyscale PNG media_image35.png 672 425 media_image35.png Greyscale ”. Regarding claim 6, Easwaran and Kawano teach the water-soluble fluorescent polymer of claim 1. Easwaran Doc#1 discloses M as: PNG media_image36.png 490 558 media_image36.png Greyscale PNG media_image37.png 320 517 media_image37.png Greyscale and thus overlaps with optionally substituted arylene or optionally substituted heteroarylene but Doc#1 does not disclose an M’ group. Doc#2 discloses a “B” group which can serve the function of an M or M’ group considering it modifies the band gap as well PNG media_image38.png 384 272 media_image38.png Greyscale . Thus, “B” as a band gap modifier could also be an optionally substituted arylene or heteroarylene of M in Doc#1 and read upon M’ as an additional unit to include. It would have been prima facie obvious to one of ordinary skill in the art, as of the effective filing date, to include an M group and further include a B group (as the M’ group) whereby both groups are chosen from the overlapping optionally substituted arylene or heteroarylene groups of Easwaran as known groups capable of modifying the bandgap of the fluorescent water soluble polymer and arrive at the invention as claimed. Thus Easwaran and Kawano teach the claimed “The water-soluble fluorescent polymer of claim 1, wherein each M and M’ is independently an optionally substituted arylene or optionally substituted heteroarylene.” Regarding claim 7, Easwaran and Kawano teach the water-soluble fluorescent polymer of claim 6. As described in the rejection of claim 6 above, Doc#1 discloses identities of M which overlap with M as claimed. Doc#2 discloses inclusion of a B group which can serve the same function as M and M’ wherein the B group modifies the polymer via modifying the band gap. Thus, any M group as disclsoed in Doc#1 would be an obvious group to pick as the B group. It would have been prima facie obvious to one of ordinary skill in the art, as of the effective filing date, to include an M group and further include a B group (as the M’ group) whereby both groups are chosen from the overlapping optionally substituted arylene or heteroarylene groups of Easwaran as known groups capable of modifying the bandgap of the fluorescent water soluble polymer and arrive at the invention as claimed. Thus Easwaran and Kawano teach the claimed “ PNG media_image39.png 719 583 media_image39.png Greyscale PNG media_image40.png 683 516 media_image40.png Greyscale PNG media_image41.png 670 552 media_image41.png Greyscale PNG media_image42.png 728 615 media_image42.png Greyscale PNG media_image43.png 216 589 media_image43.png Greyscale ”. Regarding claim 8, Easwaran and Kawano teach the water-soluble fluorescent polymer of claim 1. In Doc#1 (pg 4), Easwaran defines an optional linker L as PNG media_image44.png 131 498 media_image44.png Greyscale . In providing capping units, Easwara Doc#1 uses the molecules interchangeably with linkers (paragraph [0087]) wherein an example capping agent or linker can be: PNG media_image45.png 79 154 media_image45.png Greyscale which overlaps with the first molecule claimed: PNG media_image46.png 87 124 media_image46.png Greyscale wherein R6 is a (CH2)COOH group and n = 4. In Doc#2, Easwaran does not include linker moieties in the main chain but includes linkers in the substituents. Linkers are known to be used interchangeably and thus the overlapping identities of linkers in Doc#2 to that of Doc#1 could be reasonably implemented into the main chain of the embodiment in Doc#1 with reasonable success considering they serve the same “linker” function. In Doc#2, linkers are defined as: PNG media_image47.png 252 269 media_image47.png Greyscale . It would have been prima facie obvious to one of ordinary skill in the art, as of the effective filing date, to use the capping agent disclosed in Doc#1 as a known suitable linking agent in the embodiment of Doc#1 or choose from any of the overlapping disclosed identities of linkers across each document suitable for use in fluorescent polymers and arrive at the invention as claimed. Thus, Easwaran and Kawano teach the claimed “ PNG media_image48.png 530 610 media_image48.png Greyscale PNG media_image49.png 618 582 media_image49.png Greyscale PNG media_image50.png 182 592 media_image50.png Greyscale ”. Regarding claim 9, Easwaran and Kawano teach the water-soluble fluorescent polymer of claim 1. In Doc#1, Easwaran defines G1 and G2 (pg 4) as: PNG media_image51.png 207 510 media_image51.png Greyscale , thus matching with those defined in limitation (a) such as a substituted DHP, aryl and/or heteroaryl substituted with one or more pendant chains terminated with a functional group. As described in rejection of claim 8 above, Doc#1 also discloses a specific capping agent (which can also serve as linker) PNG media_image45.png 79 154 media_image45.png Greyscale which overlaps with the first molecule of limitation (b) claimed: PNG media_image46.png 87 124 media_image46.png Greyscale wherein R6 is a (CH2)COOH group and n = 4. Furthermore, Doc#1 (as seen in screenshot of pg4 above) discloses the capping agents are to be conjugated to a substrate or binding agent. In Doc#2, Easwaran also discloses a specific capping agent on pg14 PNG media_image52.png 97 308 media_image52.png Greyscale which overlaps with the claimed molecule in limitation (b) of PNG media_image53.png 93 228 media_image53.png Greyscale wherein n=1. It would have been prima facie obvious to one of ordinary skill in the art, as of the effective filing date, to select from any of the overlapping disclosed capping agents in either document of Easwaran as known capping agents suitable for use in fluorescent water-soluble polymers and arrive at the invention as claimed. Thus, Easwaran and Kawano teach the claimed “ PNG media_image54.png 516 579 media_image54.png Greyscale PNG media_image55.png 597 596 media_image55.png Greyscale PNG media_image56.png 240 595 media_image56.png Greyscale ”. Regarding claim 10, Easwaran and Kawano teach the water-soluble fluorescent polymer of claim 1. In paragraph [0030] of Doc#1, Easwaran teaches the entire complex of their embodiment comprises the fluorescent polymer conjugated to a binding agent (thus polymer is linked to binding agent). In paragraph [0022], Easwaran discloses the binding agent is a protein, peptide, affinity ligand, antibody, antibody fragment, sugar (thus carbohydrate), lipid, nucleic acid, or an aptamer which is identical to that of the binding agent as claimed. Thus, Easwaran and Kawano teach the claimed “The water-soluble fluorescent polymer of claim 1, further comprising a binding agent linked to said polymer, optionally wherein the binding agent is selected from the group consisting of an antibody, antibody fragment, protein, peptide, affinity ligand, carbohydrate, lipid, nucleic acid, and an aptamer.”. Regarding claim 11, Easwaran and Kawano teach the water-soluble fluorescent polymer of claim 1. In paragraph [0071] of Doc#1, Easwaran teaches the polymer has acceptor dyes attached to the backbone and depicts it linked to the linker L of the polymer on pg23 PNG media_image57.png 250 335 media_image57.png Greyscale . Thus, Easwaran and Kawano teach the claimed “The water-soluble fluorescent polymer of claim 1, further comprising an acceptor dye or chromophore linked to said polymer, optionally wherein the acceptor dye is linked to monomer A or linker L of said polymer.”. Regarding claim 12, Easwaran and Kawano teach the water-soluble fluorescent polymer of claim 1. In Fig. 5 of Doc#1, Easwaran shows excitation and emission of tandem polymers wherein excitation was carried out at polymer maxima and emissions observed from the various acceptor dyes attached to the backbone (paragraph [0029]). As described in rejections of claims 10 and 11, Easwaran teaches the entire complex of their embodiment comprises the fluorescent polymer conjugated to a binding agent (thus polymer is linked to binding agent). In paragraph [0022], Easwaran discloses the binding agent is a protein, peptide, affinity ligand, antibody, antibody fragment, sugar (thus carbohydrate), lipid, nucleic acid, or an aptamer which is identical to that of the binding agent as claimed. In paragraph [0071] of Doc#1, Easwaran teaches the polymer has acceptor dyes attached to the backbone and depicts it linked to the linker L of the polymer on pg23 PNG media_image57.png 250 335 media_image57.png Greyscale . Thus, Easwaran and Kawano teach the claimed “A tandem polymer dye comprising the water-soluble fluorescent polymer of claim 1; and an acceptor dye or chromophore linked to said polymer, optionally further comprising a binding agent linked to said polymer, optionally wherein the binding agent is selected from the group consisting of an antibody, antibody fragment, protein, peptide, affinity ligand, carbohydrate, lipid, nucleic acid, and an aptamer”. Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Easwaran et al (WO201780998A2, hereinafter Easwaran Doc#1) in view of Kawano et al (US PGPub 20140357898) and Easwaran et al (US PGPub 20200190253, hereinafter Easwaran Doc#2) as evidenced by El-Ballouli et al (NPL: “Diarylpyrenes vs diaryltetrahydropyrenes…”) as applied to claim 1 above, and further in view of Beechem et al (US PGPub 20100255487). Regarding claim 16, Easwaran and Kawano teach the fluorescent polymer of claim 1. Easwaran, in each document, teaches that water soluble fluorescent polymers can be used in a variety of biological applications by generating signals which can be monitored in real time and provide simple methods for detection of biological targets and events (paragraph [0003] Doc#1). Easwaran Doc#1 teaches that previously reported polymeric dyes utilized for such applications are highly hydrophobic and typically useful for LEDs, solar cells etc while hydrophilic or water soluble dyes are necessary to expand arsenal for use in biological applications such as in use of detecting analytes (paragraph [0005]). Beechem teaches a specific biological application requiring use of fluorescent polymers for FRET-type reactions (paragraphs [0099-0100]) which is a direct application taught by Easwaran in Doc#2 (paragraphs [0002-3]). Beechem teaches such polymers are provided in compositions, methods, systems, and kits (paragraphs [0049-51]). It would have been prima facie obvious to one of ordinary skill in the art, as of the effective filing date, to provide the water-soluble fluorescent polymer in a kit, as informed by Beechem, as a known suitable application for such fluorescent polymers in detecting analytes or real time biological events which require such hydrophilic substances, a well-known requirement for biocompatibility, and arrive at the invention as claimed. Thus, Easwaran, Kawano, and Beechem teach the claimed “A kit comprising a water soluble fluorescent polymer according to claim 1.” Conclusion The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Dose et al (WO2022013198A1) teach relevant fluorescent dyes comprising pi-conjugated based polymers and linking units. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Noa W. F. Grooms whose telephone number is (571)272-9981. The examiner can normally be reached M-F 7:30-3:30PM EST. 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, Curtis Mayes can be reached at (571) 272-1234. 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. /NWFG/Examiner, Art Unit 1759 /MELVIN C. MAYES/Supervisory Patent Examiner, Art Unit 1759