Manipulating Intramolecular Charge Transfer and Supramolecular Interaction in D-A-D Conjugated Systems by Regioisomerization.

ABSTRACT

Three new donor-acceptor-donor (D-A-D) architecture regioisomers comprising a large planar electron-withdrawing core tribenzo[a,c,i]phenazine and two identical electron-donating triphenylamines with different substitution patterns were designed and synthesized. Employing this regioisomerization strategy, the intramolecular charge-transfer interactions are effectively tuned and result in a significant bathochromic shift of photoluminescence maximum over 100 nm, which induces the corresponding emission band extending into the near-infrared region as well as giving a high solid-state quantum yield of 25%. Meanwhile, it is found that the supramolecular interactions of this series of regioisomers with planar electron-donor pyrene are greatly affected by the substitution pattern.