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Synthesis and characterization of a novel asymmetric fused ladder oligomer for applications as organic semiconductor

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Abstract

We report herein the two step synthesis of asymmetrically substituted fused heterocyclic ladder oligomer, 11-nitrobenzo[a][1,4]benzothiazino[3,-c]phenoxazine (2) and its single crystal structure. Compound 2 crystallizes in the orthorhombic space group Fdd2 with unit cell dimensions: a = 6.7497(9) Å; b = 52.478(7) Å; c = 18.832(3) Å and α = β = γ = 90°. Each unit cell contains 16 molecules. π–π Stack distances of 3.9 and 3.39 Å and short contacts of N–O…H–C distance of 2.43 Å were observed within the unit cell. Furthermore, its optical band gap was estimated be 1.85 eV. These materials are of interest for variety of applications due to their unique optical and electrical properties.

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Acknowledgments

We are very grateful for the help of Dr. Victor Young Jr. and director of the X-Ray facility at the Department of Chemistry, University of Minnesota with solving the crystal structure reported.

Funding

We would like to thank the funding from Wilkes University Department of Chemistry and Biochemistry and the Department of Electrical Engineering and Physics for funding of the project. P. Pham acknowledges support from Penn State Scranton for Professional and Research Development funding.

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Authors and Affiliations

  1. Department of Chemistry, Wilkes University, Wilkes Barre, PA, USA

    Cameron Fiester & Amy Bradley

  2. Department of Chemistry, Penn State Scranton, Dunmore, PA, USA

    Phuong-Truc T. Pham

  3. Department of Math, Physics and Computer Science, Wilkes University, Wilkes Barre, PA, USA

    Amjad Nazzal

  4. Department of Chemistry, Alfaisal University, Riyadh, Saudi Arabia

    Mamoun M. Bader

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  1. Cameron Fiester
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  2. Phuong-Truc T. Pham
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  4. Amjad Nazzal
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  5. Mamoun M. Bader
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Correspondence to Mamoun M. Bader.

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Fiester, C., Pham, PT.T., Bradley, A. et al. Synthesis and characterization of a novel asymmetric fused ladder oligomer for applications as organic semiconductor. MRS Advances 8, 889–893 (2023). https://doi.org/10.1557/s43580-023-00609-y

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