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Herein, we report a rationally designed OSC, <jats:bold>FBCF<\/jats:bold>, that synergistically combines elastic deformability, broad piezochromism, and optical waveguides via a planar benzothiadiazole (<jats:bold>BTA<\/jats:bold>) core and fluoroarene termini. The molecular architecture enforces face\u2010to\u2010face slip\u2010stacking via multiple noncovalent interactions (N\u2022\u2022\u2022H, \u03c0\u2010\u03c0, and C\u2010F\u2022\u2022\u2022\u03c0), yielding centimeter\u2010scale crystals with exceptional elastic bending and full recovery. These crystals exhibit high photoluminescence (PL) efficiency (PLQY\u00a0=\u00a075.8%) and serve as optical waveguides, maintaining performance even when bent (optical loss coefficients (OLCs): 0.286\u20130.529\u00a0dB mm<jats:sup>\u22121<\/jats:sup>). Crucially, <jats:bold>FBCF<\/jats:bold> exhibits broad pressure\u2010responsive spectral shifts (\u0394<jats:italic>\u03bb<\/jats:italic>\u00a0=\u00a0171\u00a0nm), achieving a piezochromic sensitivity of 16.7\u00a0nm GPa<jats:sup>\u22121<\/jats:sup>, exceeding that of most organic systems. Single\u2010crystal X\u2010ray diffraction analyses reveal hierarchical packing: rigid lamellar layers (stabilized by strong \u03c0\u2010\u03c0\/dipole interactions, \u2010118.56 to \u201158.45\u00a0kcal\/mol) interconnected via weaker interlayer C\u2010F\u2022\u2022\u2022\u03c0 bonds (\u221218.8\u00a0kcal\/mol). This architecture enables elastic deformation through interlayer slippage while preserving intralayer order.<\/jats:p>","DOI":"10.1002\/chem.202500888","type":"journal-article","created":{"date-parts":[[2025,3,31]],"date-time":"2025-03-31T22:31:19Z","timestamp":1743460279000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Highly Emissive Flexible Organic Crystals with Broad Piezochromism and Optical Waveguides"],"prefix":"10.1002","volume":"31","author":[{"given":"Yaya","family":"Li","sequence":"first","affiliation":[{"name":"Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry Zhejiang Normal University  Yingbin Road No. 688 Jinhua 321004 P. R. 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