Journal of Fluorescence

, Volume 26, Issue 5, pp 1805–1812 | Cite as

Comprehensive DFT and TD-DFT Studies on the Photophysical Properties of 5,6-Dichloro-1,3-Bis(2-Pyridylimino)-4,7-Dihydroxyisoindole: A New Class of ESIPT Fluorophore



Hanson et al. [Org. Lett., 2011] reported the absorption and emission spectrum of 5,6-dichloro-1,3-bis(2-pyridylimino)-4,7-dihydroxyisoindole but the excited-state intramolecular proton transfer (ESIPT) process was not investigated. The photo-physical behaviour of 5,6-dichloro-1,3-bis(2-pyridylimino)-4,7-dihydroxyisoindole was studied using the density functional theory (DFT) and time-dependent density functional theory (TD-DFT). The functional used was B3LYP and 6-31G(d) was the basis set for all the atoms. All the ten tautomers were studied for the absorption and emission properties. It is found that the tautomer where hydroxyl groups are syn to nitrogen of isoindoline ring is most stable and thus, responsible for the ESIPT process. The computed absorption and emission values of tautomers using TD-DFT are in good agreement with those obtained experimentally.


1,3-bis(2-pyridylimino) isoindoline (BPI) DFT TD-DFT ESIPT 



SK is thankful to UGC for giving study leave (FIP) and SIES college for sanctioning the study leave. PR and LR acknowledge facilities from the University of Mauritius.

Supplementary material

10895_2016_1872_MOESM1_ESM.docx (1.1 mb)
ESM 1 (DOCX 1129 kb)


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Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  1. 1.Tinctorial Chemistry Group, Department of Dyestuff TechnologyInstitute of Chemical TechnologyMumbaiIndia
  2. 2.Computational Chemistry Group, Department of Chemistry, Faculty of ScienceUniversity of MauritiusRéduitMauritius
  3. 3.Department of Pharmaceutical Chemistry, College of PharmacyKing Saud UniversityRiyadhKingdom of Saudi Arabia
  4. 4.Department of Chemistry, College of Science, Engineering and TechnologyUniversity of South AfricaPretoriaSouth Africa

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