Synthesis of some new distyrylbenzene derivatives using immobilized Pd on an NHC-functionalized MIL-101(Cr) catalyst: photophysical property evaluation, DFT and TD-DFT calculations

Esmaeil Niknam; Ali Mahmoodi; Farhad Panahi; Maryam Heydari Dokoohaki; Amin Reza Zolghadr; Ali Khalafi-Nezhad

doi:10.1039/d1ra00457c

Synthesis of some new distyrylbenzene derivatives using immobilized Pd on an NHC-functionalized MIL-101(Cr) catalyst: photophysical property evaluation, DFT and TD-DFT calculations

RSC Adv. 2021 Mar 29;11(20):12374-12380. doi: 10.1039/d1ra00457c. eCollection 2021 Mar 23.

Authors

Esmaeil Niknam¹, Ali Mahmoodi², Farhad Panahi¹, Maryam Heydari Dokoohaki¹, Amin Reza Zolghadr¹, Ali Khalafi-Nezhad¹

Affiliations

¹ Department of Chemistry, College of Sciences, Shiraz University Shiraz 71454 Iran panahi@shirazu.ac.ir panahichem@ymail.com.
² Department of Polymer Engineering and Color Technology, Amirkabir University of Technology Tehran Iran.

Abstract

In this study the catalytic application of a heterogeneous Pd-catalyst system based on metal organic framework [Pd-NHC-MIL-101(Cr)] was investigated in the synthesis of distyrylbenzene derivatives using the Heck reaction. The Pd-NHC-MIL-101(Cr) catalyst showed high efficiency in the synthesis of these π-conjugated materials and products were obtained in high yields with low Pd-contamination based on ICP analysis. The photophysical behaviors for some of the synthesized distyrylbenzene derivatives were evaluated. The DFT and TD-DFT methods were employed to determine the optimized molecular geometry, band gap energy, and the electronic absorption and emission wavelengths of the new synthesized donor-π-acceptor (D-π-A) molecules in the gas phase and in various solvents using the chemical model B3LYP/6-31+G(d,p) level of theory.