Open AccessTuning Excited-State Charge/Proton Transfer Coupled Reaction via the Dipolar Functionality
Author(s) -
PiTai Chou,
Huang,
ShihChieh Pu,
YiMing Cheng,
YiHong Liu,
Yu Wang,
ChaoTsen Chen
Publication year - 2004
Publication title -
the journal of physical chemistry a
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.756
H-Index - 235
eISSN - 1520-5215
pISSN - 1089-5639
DOI - 10.1021/jp0476390
Subject(s) - tautomer , dipole , intramolecular force , excited state , polarity (international relations) , decoupling (probability) , proton , photochemistry , chemical physics , chemistry , solvent , computational chemistry , atomic physics , stereochemistry , physics , organic chemistry , biochemistry , quantum mechanics , control engineering , engineering , cell
Based on design and synthesis of I, II, and III, we demonstrate an ingenious approach to fine-tuning the excited-state intramolecular charge transfer (ESICT) coupled excited-state intramolecular proton transfer (ESIPT) reaction via the dipolar functionality of the molecular framework. Both I and II exhibit remarkable dual emission due to the different solvent-polarity environment between ESICT and ESIPT states, while the interplay of two charge-transfer entities in III leads to ESIPT decoupling from the solvent-polarity effect, resulting in a unique proton-transfer tautomer emission. The results make further rational design of the ESICT/ESIPT coupled systems feasible simply by tuning the net dipolar effect. Accordingly, systematic investigation of the correlation in regards to the difference in dipolar vectors between ESICT and ESIPT versus solvent-polarity induced barriers becomes possible.
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