Designing of Disubstituted Derivatives of mer-Alq3: Quantum Theoretical Study

Ahmad Irfan; Ruihai Cui; Jingping Zhang; Muhammad Nadeem

doi:10.1071/CH09491

RESEARCH ARTICLE

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Designing of Disubstituted Derivatives of mer-Alq3: Quantum Theoretical Study

Ahmad Irfan ^A , Ruihai Cui ^B , Jingping Zhang ^A ^D and Muhammad Nadeem ^C

+ Author Affiliations

- Author Affiliations

^A Faculty of Chemistry, Northeast Normal University, Changchun 130024, China.

^B Department of Chemistry, Harbin University, Harbin 150080, China.

^C Formerly at Department of Chemistry, University of Agriculture, Faisalabad-38040, Punjab, Pakistan; Currently at Subsurface Technology, Petronas Research Sdn Bhd. (PRSB), Bangi-43300, Selangor, Malaysia.

^D Corresponding author. Email: zhangjingping66@yahoo.com.cn

Australian Journal of Chemistry 63(8) 1283-1289 https://doi.org/10.1071/CH09491
Submitted: 19 September 2009 Accepted: 19 March 2010 Published: 10 August 2010

Abstract

Different disubstituted derivatives of tris(8-hydroxyquinolinato)aluminium (mer-Alq3) have been designed. An electron donating group (–CH₃) has been substituted at position 4; along with electron withdrawing groups (–Cl, –CN, and –F) at position 5 (i.e. tris(4-X-5-Y-8-hydroxyquinolinato)aluminium), as well as the molecules arising from reversion of these substitutions. The designed systems have been optimized at the B3LYP/6–31G* and TD-B3LYP/6–31G* level of theories, in the ground and excited states, respectively. The absorption and emission spectra have been calculated at the TD-B3LYP/6–31G* level. A significant blue shift has been observed for tris(4-methyl-5-cyano-8-hydroxyquinolinato)aluminium (2), and red shifts for each of tris(4-methyl-5-fluoro-8-hydroxyquinolinato)aluminium (3), tris(4-chloro-5-methyl-8-hydroxyquinolinato)aluminium (4), and tris(4-cyano-5-methyl-8-hydroxyquinolinato)aluminium (5). The reorganization energy in solvent best elucidates the charge transport behaviour (p- or n-type), rather than the equivalent gas phase for mer-Alq3 and its derivatives. The reorganization energies indicate that these new derivatives have better or comparable mobility when compared to the parent molecule. The electrostatic surface potential study suggested that photostability would be enhanced. On the basis of energy decomposition analysis, we have explained the distribution pattern of frontier molecular orbitals.

Acknowledgements

Financial supports from the NSFC (No. 50873032; 20773022), NCET-06–0321, and NENU-STB07007 are gratefully acknowledged. A. Irfan acknowledges the financial support from China Scholarship Council and Ministry of Education, Pakistan.

References

Designing of Disubstituted Derivatives of mer-Alq3: Quantum Theoretical Study

Abstract

Acknowledgements

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