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Self-assembly and photoinduced electron transfer in a donor- \(\upbeta \)-cyclodextrin-acceptor supramolecular system\(^{\S }\)

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Abstract

Equimolar amounts of native \(\upbeta \)-cyclodextrin (\({\varvec{\upbeta }}\)-CD), pyrene-linked adamantane (PYAD) and tert-butylpyromellitic diimide (PMDI) when dissolved in water self-assembled to form the supramolecular donor-acceptor system \(\mathbf{PYAD}{\sqsupset }{\varvec{\upbeta }}\)-\(\mathbf{CD}{\succ }\mathbf{PMDI}\). The high affinity of adamantane derivatives for inclusion binding in the \({\varvec{\upbeta }}\)-CD cavity and the propensity of PMDI to undergo rim-binding at the narrow rim of \(\upbeta \)-CD led to the formation of \(\mathbf{PYAD}{\sqsupset }{\varvec{\upbeta }}\)-\(\mathbf{CD}{\succ }{} \mathbf{PMDI}\). The ternary complex \(\mathbf{PYAD}{\sqsupset }{\varvec{\upbeta }}\)-\(\mathbf{CD}{\succ }{} \mathbf{PMDI}\) was thoroughly characterized using various spectroscopic techniques. \(\upbeta \)-CD performs three functions in the self-assembled complex: (1) encapsulate the adamantane unit and keep the pyrene (PY) moiety above the secondary rim, (2) rim-bind PMDI and keep it at the primary rim, and (3) act as a spacer between pyrene and PMDI. Thus, the ternary complex can function as a donor-spacer-acceptor system capable of undergoing photoinduced electron transfer (PET). Upon excitation of the pyrene moiety in \(\mathbf{PYAD}{\sqsupset }{\varvec{\upbeta }}\)-\(\mathbf{CD}{\succ }{} \mathbf{PMDI}\) an electron is transferred from the excited pyrene to the PMDI ground state. Steady state and time resolved fluorescence experiments were carried out to study the PET in \(\mathbf{PYAD}{\sqsupset }{\varvec{\upbeta }}\)-\(\mathbf{CD}{\succ }{} \mathbf{PMDI}\). Existence of the ternary system and PET processes taking place within it are further supported by laser flash photolysis experiments.

Graphical abstract \(\upbeta \)-CD assembles donor pyrene through inclusion binding and acceptor pyromellitic diimide through rim-binding. Fluorescence intensity and lifetime quenching suggested photoinduced electron transfer from pyrene to pyromellitic diimide.

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Acknowledgements

The authors thank DAE-BRNS (No. 2007/37/37/BRNS), and CSIR for financial support. R.K. and S. B. K. are grateful to CSIR for fellowships. This is contribution number NIIST-PPG 348.

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  1. Retheesh Krishnan

    Present address: Department of Chemistry, Government College for Women, Thiruvananthapuram, 695 014, Kerala, India

  2. Bijitha Balan

    Present address: Department of Chemistry, Government College Kariavattom, Thiruvananthapuram, 695 581, Kerala, India

Authors and Affiliations

  1. Photosciences and Photonics, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Council of Scientific and Industrial Research, Thiruvananthapuram, 695 019, Kerala, India

    Retheesh Krishnan, Sumesh Babu Krishnan, Bijitha Balan & Karical Raman Gopidas

  2. Academy of Scientific and Innovative Research (AcSIR), New Delhi, 110 001, India

    Sumesh Babu Krishnan & Karical Raman Gopidas

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$$^{\S }$$ § Dedicated to Professor M. V. George on the occasion of his 90 $$^\mathrm{th}$$ th Birth Anniversary.

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Krishnan, R., Krishnan, S.B., Balan, B. et al. Self-assembly and photoinduced electron transfer in a donor- \(\upbeta \)-cyclodextrin-acceptor supramolecular system\(^{\S }\). J Chem Sci 130, 134 (2018). https://doi.org/10.1007/s12039-018-1535-z

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