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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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