The elevation of the chemotherapeutic efficacy and attenuation of its side effects on healthy cells and tissues become one of the prime targets for the treatment of cancer. Toward this direction, a sequential receptor and mitochondria dual-targeting strategy was implemented in the DX TP PG BN 19 F theranostic polymer that was anchored with the chemotherapeutic agent doxorubicin, receptor-targeting biotin, and mitochondria-targeting triphenylphosphonium cations. The polymer was flourished with a unique 19F magnetic resonance imaging (MRI) tracer that exhibited high segmental mobility and eventually led to prolonged T 2 relaxation time. Furthermore, for the sake of amphiphilicity, the DX TP PG BN 19 F polymer spontaneously aggregated into nano-sphere with positive zeta potential, where the MRI tracer and biotin embedded at the exterior and displayed site-specific targeting and remarkable 19F MRI capability simultaneously. The mitochondria-targeting competency of the DX TP PG BN 19 F theranostic polymer was investigated by comparing the non-mitochondrial-targeting DX PG BN 19 F polymer using fluorescence microscopic cell imaging in human cervical, HeLa, and breast MCF-7 carcinoma cell lines. Moreover, cytotoxicity experiments of the aforementioned theranostic polymers clarified the enhancement of the chemotherapeutic efficacy of DX TP PG BN 19 F theranostic polymers through effective and precise mitochondrial doxorubicin delivery that forced to follow the apoptotic path.

Here, we reported a unique twisted rod‐like nano‐architecture of as‐synthesized 4‐fluorocinnmaoyl chloride derived polynorbornene (PNORCNF) on the addition of 1‐pyrenemethanol (PM) as a sensing probe. A significant change in the PNORCNF/PM microenvironment's polarity was observed with increasing PM concentration keeping the solvent (THF) unaltered. The change in polarity could be well documented with the morphological changes of the PNORCNF/PM system. We proposed π‐π interaction between PM and cinnamoyl moiety of PNORCNF for this type of well‐controlled hierarchical self‐aggregation.