{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,21]],"date-time":"2026-10-21T17:08:46Z","timestamp":1792602526122,"version":"4.5.0"},"reference-count":46,"publisher":"American Chemical Society (ACS)","issue":"43","license":[{"start":{"date-parts":[[2022,10,19]],"date-time":"2022-10-19T00:00:00Z","timestamp":1666137600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/100007237","name":"University of North Dakota","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007237","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["P20GM113123"],"award-info":[{"award-number":["P20GM113123"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["U54GM128729"],"award-info":[{"award-number":["U54GM128729"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["1946202"],"award-info":[{"award-number":["1946202"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE 1709160"],"award-info":[{"award-number":["CHE 1709160"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2022,11,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Red and near-infrared emission is a highly desirable feature for fluorescent nanoparticles in biological applications mainly due to longer wavelengths more easily being able to deeply penetrate tissues, organs, skin, and other organic components, while less autofluorescence interference would be produced. Additionally, graphene quantum dots (GQDs) that contain unique optical and electrical features have been targeted for their use in cell labeling applications as well as environmental analysis. Their most desirable features come in the form of low toxicity and biocompatibility; however, GQDs are frequently reported to have blue or green emission light and not the more advantageous red\/NIR emission light. Furthermore, porphyrins are a subgroup of heterocyclic macrocycle organic compounds that are also naturally occurring pigments in nature that already contain the desired red-emission fluorescence. Therefore, porphyrins have been used previously to synthesize nanomaterials and for nanoparticle doping in order to incorporate the red\/NIR emission light property into particles that otherwise do not contain the desired emission light. Meso-tetra\u00ad(4-carboxyphenyl)\u00adporphine (TCPP) is one type of porphyrin with a large conjugated \u03c0-electron system and four carboxyl groups on its exterior benzene rings. These two key characteristics of TCPP make it ideal for incorporation into GQDs, as it would design and synthesize red-emissive material as well as give rise to excellent water solubility. In this work, TCPP is used in tangent with cis-cyclobutane-1,2-dicarboxylic acid (CBDA-2), a biomass derived organic molecule, to synthesize \u201cgreen\u201d porphyrin-based graphene quantum dots (PGQDs) with red-emission. The obtained PGQDs were characterized by various analytical methods. Utilizing TEM, HRTEM, and DLS the size distribution of the particles was determined to be 7.9 \u00b1 4.1, well within the quantum dot range of 2\u201310 nm. FT-IR, XPS, and XRD depicted carbon, nitrogen, and oxygen as the main elemental components with carbon being in the form of graphene and the main porphyrin ring of TCPP remaining present in the final PGQDs product. Lastly, absorption and fluorescence spectroscopy determined the excitation wavelength at 420 nm and the emission at 650 nm which was successfully utilized in the imaging of HeLa cells using confocal microscopy.<\/jats:p>","DOI":"10.1021\/acsomega.2c04623","type":"journal-article","created":{"date-parts":[[2022,10,19]],"date-time":"2022-10-19T16:46:47Z","timestamp":1666198007000},"page":"38902-38911","source":"Crossref","is-referenced-by-count":9,"title":["Development of\nRed-Emissive Porphyrin Graphene Quantum\nDots (PGQDs) for Biological Cell-Labeling Applications"],"prefix":"10.1021","volume":"7","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2873-0040","authenticated-orcid":true,"given":"Sarah","family":"Reagen","sequence":"first","affiliation":[{"name":"University of North Dakota , , , ,","place":["Grand Forks, North Dakota, United States, 58202"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yingfen","family":"Wu","sequence":"additional","affiliation":[{"name":"University of North Dakota , , , ,","place":["Grand Forks, North Dakota, United States, 58202"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rahul","family":"Shahni","sequence":"additional","affiliation":[{"name":"University of North Dakota , , , ,","place":["Grand Forks, North Dakota, United States, 58202"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4172-5177","authenticated-orcid":true,"given":"Wen","family":"Sun","sequence":"additional","affiliation":[{"name":"University of North Dakota , , , ,","place":["Grand Forks, North Dakota, United States, 58202"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jin","family":"Zhang","sequence":"additional","affiliation":[{"name":"University of North Dakota , , , ,","place":["Grand Forks, North Dakota, United States, 58202"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qianli R.","family":"Chu","sequence":"additional","affiliation":[{"name":"University of North Dakota , , , ,","place":["Grand Forks, North Dakota, United States, 58202"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7794-979X","authenticated-orcid":true,"given":"Xiaodong","family":"Hou","sequence":"additional","affiliation":[{"name":"University of North Dakota , , , ,","place":["Grand Forks, North Dakota, United States, 58202"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Colin","family":"Combs","sequence":"additional","affiliation":[{"name":"University of North Dakota , , , ,","place":["Grand Forks, North Dakota, United States, 58202"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9603-666X","authenticated-orcid":true,"given":"Julia Xiaojun","family":"Zhao","sequence":"additional","affiliation":[{"name":"University of North Dakota , , , ,","place":["Grand Forks, North Dakota, United States, 58202"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2022,10,19]]},"reference":[{"key":"2026081709223018700_cit1","doi-asserted-by":"publisher","first-page":"157","DOI":"10.1515\/ntrev-2017-0199","article-title":"Synthesis\nand applications of graphene quantum dots: a review","volume":"7","author":"Chen","year":"2018","journal-title":"Nanotechnol Rev."},{"key":"2026081709223018700_cit2","doi-asserted-by":"publisher","first-page":"944","DOI":"10.3390\/nano8110944","article-title":"Biomedical applications of graphene-based\nstructures","volume":"8","author":"Tadyszak","year":"2018","journal-title":"Nanomaterials."},{"key":"2026081709223018700_cit3","doi-asserted-by":"publisher","first-page":"25865","DOI":"10.1021\/acsami.5b08226","article-title":"Modification\nof structural and luminescence properties of graphene quantum dots\nby gamma irradiation and their application in a photodynamic therapy","volume":"7","author":"Jovanovic\u0301","year":"2015","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"2026081709223018700_cit4","doi-asserted-by":"publisher","first-page":"1072","DOI":"10.3390\/s20041072","article-title":"Applications of graphene\nquantum dots in biomedical\nsensors","volume":"20","author":"Mansuriya","year":"2020","journal-title":"Sensors."},{"key":"2026081709223018700_cit5","doi-asserted-by":"publisher","first-page":"1696","DOI":"10.3390\/ijms19061696","article-title":"Graphene quantum\ndots and enzyme-coupled biosensors for highly sensitive determination\nof hydrogen peroxide and glucose","volume":"19","author":"Wang","year":"2018","journal-title":"Int. J. Mol.\nSci."},{"key":"2026081709223018700_cit6","doi-asserted-by":"publisher","first-page":"847","DOI":"10.1007\/s10895-021-02712-5","article-title":"Functionalized\ngraphene quantum dots for cholesterol detection in human blood serum","volume":"31","author":"Ayilliath","year":"2021","journal-title":"J. Fluoresc."},{"key":"2026081709223018700_cit7","doi-asserted-by":"publisher","first-page":"46336","DOI":"10.1007\/s11356-020-07891-5","article-title":"Synthesis of highly fluorescent and water soluble graphene\nquantum dots for detection of heavy metal ions in aqueous media","volume":"28","author":"Raj","year":"2021","journal-title":"Envir. Sci. Pollut. Res. Int."},{"key":"2026081709223018700_cit8","doi-asserted-by":"publisher","first-page":"111642","DOI":"10.1016\/j.msec.2020.111642","article-title":"Preparation\nof blue- and green-emissive\nnitrogen-doped graphene quantum dots from graphite and their application\nin bioimaging","volume":"119","author":"Shah","year":"2021","journal-title":"Mater. Sci. Eng. 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Interfaces."},{"key":"2026081709223018700_cit25","doi-asserted-by":"publisher","first-page":"4086","DOI":"10.7150\/thno.25433","article-title":"Ultrathin Cu-TCPP MOF nanosheets:\na new theragnostic nanoplatform with magnetic resonance\/near-infrared\nthermal imaging for synergistic phototherapy of cancers","volume":"8","author":"Li","year":"2018","journal-title":"Theranostics."},{"key":"2026081709223018700_cit26","doi-asserted-by":"publisher","first-page":"12567","DOI":"10.1021\/acsomega.9b00980","article-title":"Meso-tetra (4-carboxylphenyl)\u00adporphine-enhanced\nDNA methylation sensing interface on a light-addressable potentiometric\nsensor","volume":"4","author":"Jia","year":"2019","journal-title":"ACS Omega."},{"key":"2026081709223018700_cit27","doi-asserted-by":"publisher","first-page":"8136","DOI":"10.1021\/acssuschemeng.8b02415","article-title":"Fufural-derived\ndiacid prepared by photoreaction for sustainable materials synthesis","volume":"6","author":"Wang","year":"2018","journal-title":"ACS Sustain. 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Bioelectron."},{"key":"2026081709223018700_cit43","doi-asserted-by":"publisher","first-page":"109802","DOI":"10.1016\/j.dyepig.2021.109802","article-title":"A novel fluorescent\nmetal-organic framework based on porphyrin and AIE for ultra-high\nsensitivity and selectivity detection of Pb2+ ions in aqueous\nsolution","volume":"196","author":"Wang","year":"2021","journal-title":"Dyes Pigm."},{"key":"2026081709223018700_cit44","doi-asserted-by":"publisher","first-page":"108967","DOI":"10.1016\/j.dyepig.2020.108967","article-title":"Ultra-thin\nfilm sensors based on porphyrin-5-ylphosphonate diesters for selective\nand sensitive dual-channel optical detection of mercury (II) ions","volume":"186","author":"Ermakova","year":"2021","journal-title":"Dyes Pigm."},{"key":"2026081709223018700_cit45","doi-asserted-by":"publisher","first-page":"1116","DOI":"10.1021\/acs.inorgchem.0c03268","article-title":"Porphyrin-based metal-organic\nframework probe: highly selective and sensitive fluorescent turn-on\nsensor for M3+ (Al3+, Cr3+, and Fe3+) ions","volume":"60","author":"Fu","year":"2021","journal-title":"Inorg. 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Sci."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.2c04623","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/7\/43\/38902\/4183412\/ao2c04623.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/7\/43\/38902\/4183412\/ao2c04623.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T13:24:27Z","timestamp":1786973067000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/7\/43\/38902\/414128\/Development-of-Red-Emissive-Porphyrin-Graphene"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,10,19]]},"references-count":46,"journal-issue":{"issue":"43","published-online":{"date-parts":[[2022,10,19]]},"published-print":{"date-parts":[[2022,11,1]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.2c04623","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,10,19]]}}}