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Photophysical Behavior and Computational Investigation of Novel 1,4-Bis(2-(2-Phenylpyrimido[1,2-a]Benzimidazol-4-Yl)Phenoxy)Butan (BPPB) Macromolecule

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Abstract

A new macromolecule pyrimido[l,2-a]benzimidazole derivative named 1,4-bis(2-(2-phenylpyrimido[1,2-a]benzimidazol-4-yl)phenoxy)butan (BPPB) has been synthesized in accepted yield using microwave assistance. The new compound BPPB has been formed by the interaction of 3,3′-((butane-1,4-diylbis(oxy))bis(2,1-phenylene))bis(1-phenylprop-2-en-1-one) (3) with 2- aminobenzimidazole (4) in the presence of potassium hydroxide as a basic catalyst in dimethylformamide (DMF) under microwave radiation for 20 min. The chemical structure of this novel compound was elucidated by elemental and spectral techniques including: FT-IR, 1H-NMR, 13C-NMR and mass spectra. The electronic absorption and emission spectra of BPPB were measured in different solvents. BPPB displayed a solvatochromic effect of the emission spectrum that is reflected by red shifts of its fluorescence emission maxima on increasing the solvent polarity, indicating a change of electronic charge distribution upon excitation. BPPB crystalline solids gave excimer-like emission at 535 nm with a bandwidth of ca. 60 nm. Ground and excited states electronic geometry optimizations using density functional theory (DFT) and time-dependent density functional theory (TD-DFT), respectively, complemented these spectral findings. The intramolecular charge transfer was investigated by natural bond orbital (NBO) technique.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Jeddah University, Jeddah, 80327, Saudi Arabia

    Tamer S. Saleh, Khalid A. Alamry & Ahmed E. M. Mekky

  2. Green Chemistry Department, National Research Centre, Dokki, Cairo, 12622, Egypt

    Tamer S. Saleh

  3. Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia

    Mahmoud A. Hussein, Osman I. Osman, Khalid A. Alamry & Abdullah M. Asiri

  4. Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt

    Mahmoud A. Hussein

  5. Chemistry Department, Faculty of Science, Khartoum University, P.O. Box 321, 11111, Khartoum, Sudan

    Osman I. Osman

  6. Chemistry Department, Faculty of Science, Cairo University, Giza, 12613, Egypt

    Ahmed E. M. Mekky

  7. Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah, 21589, P.O. Box 80203, Saudi Arabia

    Abdullah M. Asiri

  8. Chemistry Department, Faculty of Science, Tanta University, Tanta, 2173, Egypt

    Samy A. El-Daly

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  1. Tamer S. Saleh
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Saleh, T.S., Hussein, M.A., Osman, O.I. et al. Photophysical Behavior and Computational Investigation of Novel 1,4-Bis(2-(2-Phenylpyrimido[1,2-a]Benzimidazol-4-Yl)Phenoxy)Butan (BPPB) Macromolecule. J Fluoresc 26, 1895–1904 (2016). https://doi.org/10.1007/s10895-016-1884-2

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