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All dyes have a quadrupolar, centrosymmetric architecture and two five\u2010membered rings adjacent to a central electron\u2010rich DHPP core, but they differ in the strength of peripheral electron\u2010withdrawing functionalities and degree of deviation from planarity. Ketones exhibit charge\u2010transfer (CT) bands located between 500\u2013600\u00a0nm and vanishingly weak emission, whereas dyes possessing dicyanovinylidene functionality and \u03c0\u2010expanded chromophore feature complex absorption spectra with CT bands beyond 700\u00a0nm. Computational studies enabled assignment of absorption bands to intramolecular charge\u2010transfer and higher\u2010energy \u03c0\u2013\u03c0* transitions. The lack of emission was rationalized by invoking efficient nonradiative decay arising from internal conversion and\/or intersystem crossing (DHPP possessing four bromine atoms). The two\u2010photon absorption cross\u2010section reaches up to 240 GM for the most strongly polarized and twisted donor\u2010acceptor DHPP system. All the synthesized dyes proved to be good photosensitizers in two\u2010photon induced polymerization, with the twisted DHPP derivative exhibiting a polymerization threshold as low as 130\u00a0GW\/cm\n                    <jats:sup>2<\/jats:sup>\n                    , nearly an order of magnitude lower than those of conventional photosensitizers.\n                  <\/jats:p>","DOI":"10.1002\/chem.71810","type":"journal-article","created":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T03:42:56Z","timestamp":1792726976000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Highly Polarized 1,4\u2010Dihydropyrrolo[3,2\u2010\n                    <i>b<\/i>\n                    ]Pyrroles: From Synthesis to Photophysics and Two\u2010Photon Induced Polymerization"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0009-0001-1141-7501","authenticated-orcid":false,"given":"Krzysztof J.","family":"Kochanowski","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry Polish Academy of Sciences  Warsaw Poland"},{"name":"Inter\u2010faculty Individual Studies in Mathematics and Natural Sciences University of Warsaw  Warsaw Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5030-8888","authenticated-orcid":false,"given":"Yuri","family":"Tanuma","sequence":"additional","affiliation":[{"name":"Department of Science and Technology Link\u00f6ping University, Laboratory of Organic Electronics  Norrk\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2088-2608","authenticated-orcid":false,"given":"Rashid","family":"Valiev","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Helsinki  Helsinki Finland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-3474-5514","authenticated-orcid":false,"given":"Michalis","family":"Stavrou","sequence":"additional","affiliation":[{"name":"Foundation for Research and Technology\u2010Hellas (FORTH) Institute of Electronic Structure and Laser  Heraklion Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David","family":"Gray","sequence":"additional","affiliation":[{"name":"Foundation for Research and Technology\u2010Hellas (FORTH) Institute of Electronic Structure and Laser  Heraklion Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2435-4156","authenticated-orcid":false,"given":"Maria","family":"Farsari","sequence":"additional","affiliation":[{"name":"Foundation for Research and Technology\u2010Hellas (FORTH) Institute of Electronic Structure and Laser  Heraklion Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0716-3385","authenticated-orcid":false,"given":"Glib","family":"Baryshnikov","sequence":"additional","affiliation":[{"name":"Department of Science and Technology Link\u00f6ping University, Laboratory of Organic Electronics  Norrk\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2146-1282","authenticated-orcid":false,"given":"Daniel T.","family":"Gryko","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry Polish Academy of Sciences  Warsaw Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,10,22]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b11829"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c01665"},{"key":"e_1_2_8_4_1","doi-asserted-by":"crossref","DOI":"10.1002\/0470084960","volume-title":"March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure","author":"Smith M. 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