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Molecules 2013, 18(8), 9603-9622; doi:10.3390/molecules18089603
Article

Synthesis of Photoresponsive Dual NIR Two-Photon Absorptive [60]Fullerene Triads and Tetrads

1, 1, 2, 2, 3,4 and 1,*
1 Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts, Lowell, MA 01854, USA 2 AFRL/RXAS, Functional Materials Division, Air Force Research Laboratory, Wright-Patterson Air Force Base, Dayton, OH 45433, USA 3 Wellman Center for Photomedicine, Massachusetts General Hospital, Department of Dermatology, Harvard Medical School, Boston, MA 02114, USA 4 Harvard MIT Division of Health Science and Technology, Cambridge, MA 02139, USA
* Author to whom correspondence should be addressed.
Received: 18 June 2013 / Revised: 30 July 2013 / Accepted: 5 August 2013 / Published: 12 August 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

Broadband nonlinear optical (NLO) organic nanostructures exhibiting both ultrafast photoresponse and a large cross-section of two-photon absorption throughout a wide NIR spectrum may make them suitable for use as nonlinear biophotonic materials. We report here the synthesis and characterization of two C60-(antenna)x analogous compounds as branched triad C60(>DPAF-C18)(>CPAF-C2M) and tetrad C60(>DPAF-C18)(>CPAF-C2M)2 nanostructures. These compounds showed approximately equal extinction coefficients of optical absorption over 400–550 nm that corresponds to near-IR two-photon based excitation wavelengths at 780–1,100 nm. Accordingly, they may be utilized as potential precursor candidates to the active-core structures of photosensitizing nanodrugs for 2γ-PDT in the biological optical window of 800–1,050 nm.
Keywords: C60-(antenna)x nanostructures; ultrafast intramolecular energy-transfer; NIR two-photon absorption; 2γ-photodynamic therapeutic agent; photosensitizer C60-(antenna)x nanostructures; ultrafast intramolecular energy-transfer; NIR two-photon absorption; 2γ-photodynamic therapeutic agent; photosensitizer
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Jeon, S.; Wang, M.; Tan, L.-S.; Cooper, T.; Hamblin, M.R.; Chiang, L.Y. Synthesis of Photoresponsive Dual NIR Two-Photon Absorptive [60]Fullerene Triads and Tetrads. Molecules 2013, 18, 9603-9622.

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