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Self-assembly characteristics of a multipolar donor-acceptor–based bis-pyrene integrated molecular tweezer

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Abstract

A modular design of a molecular tweezer is presented that integrates a multipolar D- π-A [D: Donor, A: Acceptor] scaffold, 1-aminopyrene-based fluorophore units and L-alanine-based linkers. The synthesis of the molecule is based on two-fold aromatic nucleophilic reactions (ArSN) and coupling reactions of the acid and amino functionalities. This molecule crystallizes in a non-centrosymmteric (P21) space group. We present its rich self-assembly characteristics that involves an array of π-stacking interactions. In addition, the molecular tweezer within its cleft forms H-bonding with two dimethylformamide molecules. Such multipolar D- π-A systems containing chiral and fluorophore units are potential candidates for a number of electronic and photonic applications.

Self-assembly of a multipolar scaffold having chiral units and flurophores was observed and characterized.

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Acknowledgements

We acknowledge DBT BUILDER, DST PURSE for the funding and the central instrumentation facility at AIRF, JNU for IR, Mass and NMR studies.

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Authors and Affiliations

  1. Supramolecular & Material Chemistry Lab, School of Physical Sciences, Jawaharlal Nehru University, New Delhi, 110067, India

    DEEPAK ASTHANA, GEETA HUNDAL & PRITAM MUKHOPADHYAY

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  1. DEEPAK ASTHANA
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  2. GEETA HUNDAL
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  3. PRITAM MUKHOPADHYAY
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Correspondence to PRITAM MUKHOPADHYAY.

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Supplementary Information

The detailed procedure for synthesis and characterization, MALDITOF Mass, IR, 1H and 13C, DEPT-135, APT NMR spectra, X-ray crystallographic tables are given in SI file available at www.ias.ac.in/chemsci.

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ASTHANA, D., HUNDAL, G. & MUKHOPADHYAY, P. Self-assembly characteristics of a multipolar donor-acceptor–based bis-pyrene integrated molecular tweezer. J Chem Sci 126, 1331–1336 (2014). https://doi.org/10.1007/s12039-014-0687-8

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  • DOI: https://doi.org/10.1007/s12039-014-0687-8

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