A chiral, highly polar, multichromophoric supermolecule has been designed by gathering seven push-pull chromophores onto a beta-cyclodextrin assembling unit through covalent flexible linkers. The photophysical and nonlinear optical properties of this mutichromophoric conical bundle were investigated and compared with those of the monomeric chromophore. The strongly absorbing multichromophoric system combines interesting features: it has a high molecular first-order hyperpolarisability and a very large dipolar moment (u = 38 D) which reveal a self-arrangement of the dipolar chromophores within the supermolecule. The confinement of the push-pull chromophores within the nanoscopic bundle affects their optical properties and promotes interactions: the multichromophoric supermolecule is hypochromically and hypsochromically shifted with respect to its monomeric analogue. In addition, the close proximity promotes excitonic coupling, as well as excimer formation phenomena.