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.
Highlights
Fullerenes are nanocarbon cages with all sp2 carbons interlinked in a structure of hollow sphere.Highly strained curving regions of the cage surface consist of chemically reactive six fulvalenyl bridging olefins that can be utilized for making nucleophilic addition reactions
diphenylaminofluorene 5 (DPAF)-Cn)x, capable of exhibiting photoresponse in a nearly instantaneous time scale to protect against high-intensity radiation
Upon the chemical alteration of the keto group of C60(>DPAF-Cn) bridging between C60 and the antenna moiety to a highly electron-withdrawing 1,1-dicyanoethylenyl (DCE) group, it was possible to extend the π-conjugation in the resulting C60(>CPAF-Cn) analogous chromophore molecules to a close contact with the cage current
Summary
Fullerenes are nanocarbon cages with all sp carbons interlinked in a structure of hollow sphere. We report the synthesis and spectroscopic characterization of photoresponsive dual NIR two-photon absorptive [60]fullerene triads and tetrads using the extended synthetic method for the preparation of their corresponding monoadduct analogous C60(>DPAF-C18) 1 and C60(>CPAF-C2M) 2, as shown in Scheme 1. These triads and tetrads are capable of undergoing 2PA-based photoexcitation process at either 780 or 980 nm making them potential precursor candidates to the active-core structures of nanodrugs for 2γ-PDT
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