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Herein we report a one\u2010shot Pd(II)\u2010catalyzed multiple C\u2013H activation strategy that enables modular access to fluorenylidene\/oxindole\u2010based MPAEs through intramolecular diarylation of\n                    <jats:italic>N<\/jats:italic>\n                    \u2010aryl amide\u2010tethered biarylalkynes. The synergistic PdCl\n                    <jats:sub>2<\/jats:sub>\n                    \/PivOH\/MnO\n                    <jats:sub>2<\/jats:sub>\n                    system promotes sequential C\u2013H activation\/alkyne insertion\/C\u2013H activation under mild conditions, furnishing mono\u2010, di\u2010, and tri\u2010olefin\u2010bridged frameworks in good to high yields. Mechanistic investigations, including kinetic isotope effect measurements and DFT calculations, indicate that the\n                    <jats:italic>syn<\/jats:italic>\n                    \u2010alkyne insertion step is likely rate\u2010determining, whereas the C\u2013H activation steps proceed through a pivalate\u2010assisted concerted metalation\u2013deprotonation (CMD) pathway. The method allows rapid assembly of densely conjugated, nonplanar \u03c0\u2010systems from simple linear precursors, including multiple annulations that proceed in a single operation. The resulting 3D \u03c0\u2010architectures display broad and bathochromically shifted absorptions (\n                    <jats:italic>\u03bb<\/jats:italic>\n                    <jats:sub>onset<\/jats:sub>\n                    up to 820\u00a0nm), tunable frontier orbital energies, and donor\u2013acceptor electronic structures modulated by \u03c0\u2010extension and heteroatom incorporation. This modular C\u2013H activation platform provides efficient entry to structurally diverse, narrow optical gap MPAEs and expands the synthetic toolbox for advanced optoelectronic \u03c0\u2010materials.\n                  <\/jats:p>","DOI":"10.1002\/chem.71221","type":"journal-article","created":{"date-parts":[[2026,6,30]],"date-time":"2026-06-30T09:56:52Z","timestamp":1782813412000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["One\u2010Shot Pd(II)\u2010Catalyzed Multiple C\u2013H Activation Enables Modular Construction of Fluorenylidene Oxindole\u2010Based Multi(Polycyclic) Aromatic Enes"],"prefix":"10.1002","volume":"32","author":[{"given":"Haiyu","family":"Wang","sequence":"first","affiliation":[{"name":"Department of Chemistry, Graduate School of Science Tohoku University  Sendai 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