Optical properties of the dibenzothiazolylphenol molecular crystals through ONIOM calculations: the effect of the electrostatic embedding scheme

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• 作者：Davide Presti ; Alfonso Pedone ; Ilaria Ciofini…
• 关键词：ESIPT fluorophores ; Molecular crystals ; TD ; DFT ; ONIOM ; Electrostatic embedding
• 刊名：Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta)
• 出版年：2016
• 出版时间：April 2016
• 年：2016
• 卷：135
• 期：4
• 全文大小：1,435 KB
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• 作者单位：Davide Presti (1)
  Alfonso Pedone (1)
  Ilaria Ciofini (2)
  Frédéric Labat (2)
  Maria Cristina Menziani (1)
  Carlo Adamo (2) (3)
  
  1. Dipartimento di Scienze Chimiche e Geologiche, Università di Modena e Reggio-Emilia, via G. Campi 103, 41125, Modena, Italy
  2. PSL Research University, Institut de Recherche de Chimie Paris, CNRS Chimie ParisTech, 11 rue P. et M. Curie, 75005, Paris, France
  3. Institut Universitaire de France, 103 Boulevard Saint Michel, 75005, Paris, France
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Theoretical and Computational Chemistry
  Inorganic Chemistry
  Organic Chemistry
  Physical Chemistry
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1432-2234

文摘

Periodic density functional theory (DFT) and hybrid ONIOM time-dependent DFT/MM cluster calculations have been carried out to investigate the ground- and excited-state properties of the crystalline structures of the enolic and ketonic tautomeric forms of a propoxy-substituted dibenzothiazolylphenol molecule (OPr), a prototype for systems undergoing the excited-state intramolecular proton transfer process. The crystalline structures of the tautomeric forms are well reproduced and, as expected, at the ground state, the enol polymorph is predicted to be more stable than the keto one. At the excited state, the effect of the environment on time-dependent DFT calculations has been accounted for by including a charge embedding scheme, and the influence of different kinds of point charges (Mulliken, CM5, RESP and Q _Eq) in determining the optical properties of the central molecule has been investigated. The results reveal that, in fair agreement with experimental data, the absorption (emission) energies of the enol (keto) OPr molecule is red-shifted of about 3 (3) nm going from the gas phase to chloroform and blue-shifted of 10 (23) nm going from the gas to the crystal phase when the electronic embedding with Mulliken charges is employed. The electrostatic embedding influences the excited-state properties more severely than the ground-state properties, and apart the Q _Eq charges, all other models provide Stokes shifts in reasonable agreement with experimental data.