Quantitative Design of Bright Fluorophores and AIEgens by the Accurate Prediction of Twisted Intramolecular Charge Transfer (TICT)
Top Cited Papers
- 15 June 2020
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 59 (25), 10160-10172
- https://doi.org/10.1002/anie.201916357
Abstract
Inhibition of TICT can significantly increase the brightness of fluorescent materials. Accurate prediction of TICT is thus critical for the quantitative design of high-performance fluorophores and AIEgens. TICT of 14 types of popular organic fluorophores were modeled with time-dependent density functional theory (TD-DFT). A reliable and generalizable computational approach for modeling TICT formations was established. To demonstrate the prediction power of our approach, we quantitatively designed a boron dipyrromethene (BODIPY)-based AIEgen which exhibits (almost) barrierless TICT rotations in monomers. Subsequent experiments validated our molecular design and showed that the aggregation of this compound turns on bright emissions with ca. 27-fold fluorescence enhancement, as TICT formation is inhibited in molecular aggregates.Funding Information
- Singapore University of Technology and Design (T1SRCI17126; IDG31800104)
- National Natural Science Foundation of China (21878286, 21908216)
This publication has 91 references indexed in Scilit:
- 2,5-PRODAN: synthesis and propertiesPhotochemical & Photobiological Sciences, 2011
- Does PRODAN Possess an O-TICT Excited State? Synthesis and Properties of Two Constrained DerivativesThe Journal of Physical Chemistry A, 2010
- A multistate local coupled cluster CC2 response method based on the Laplace transformThe Journal of Chemical Physics, 2009
- Accurate Simulation of Optical Properties in DyesAccounts of Chemical Research, 2008
- New Insights on the Photophysical Behavior of PRODAN in Anionic and Cationic Reverse Micelles: From Which State or States Does It Emit?The Journal of Physical Chemistry B, 2007
- Does PRODAN Possess a Planar or Twisted Charge-Transfer Excited State? Photophysical Properties of Two PRODAN DerivativesThe Journal of Physical Chemistry A, 2003
- Structural Changes Accompanying Intramolecular Electron Transfer: Focus on Twisted Intramolecular Charge-Transfer States and StructuresChemical Reviews, 2003
- Shedding Light on Excited-State Structures by Theoretical Analysis of Femtosecond Transient Infrared Spectra: Intramolecular Charge Transfer in 4-(Dimethylamino)benzonitrileJournal of the American Chemical Society, 2000
- Photophysical and Dynamic NMR Studies on 4-Amino-7-nitrobenz-2-oxa-1, 3-diazole Derivatives: Elucidation of the Nonradiative Deactivation PathwayThe Journal of Physical Chemistry A, 1998
- Ladungstrennung in angeregten Zuständen entkoppelter Systeme – TICT-Verbindungen und Implikationen für die Entwicklung neuer Laserfarbstoffe sowie für den Primärprozeß von Sehvorgang und PhotosyntheseAngewandte Chemie, 1986