Ladder-Type Dye with Large Transition Dipole Moment for Solvatochromism and Microphase Visualization.

A large transition dipole moment is usually pursued by strategies of twisted intramolecular charge transfer (TICT) or planar intramolecular charge transfer (PICT) to obtain obvious Stokes shifts and dramatic color changes with tuning of polarities. However, both strategies have their drawbacks and suffer from fluorescence quenching in solid states. Herein, a ladder-type molecule ISOAA-H with an intramolecular hydrogen bond is designed, which undergoes intramolecular charge transfer and proton shift to harvest a large transition dipole moment under light irradiation. Thanks to its out-of-plane side chains, the intermolecular π-π stacking of backbones is prohibited and solid emission is generated. ISOAA-H exhibits outstanding solvatochromic behavior with polarity changes of solvents or polymer matrixes and is successfully used to detect the microphase separation of polymer blends. These results indicate that a strategy combining the advantages of TICT and PICT is established for environment-sensitive dyes used in both solution and solid state.