“Push-no-pull” porphyrins for second harmonic generation imaging

Abstract

The established approach to design a molecule with strong second-order nonlinear optical (NLO) activity is to connect an electron-donor to an electron-acceptor via a p-conjugated bridge, to generate push-pull system. Surprisingly, we have found that dyes with large first hyperpolarizabilities, and which exhibit strong second harmonic generation (SHG), can be created just by attaching an electron-donor to a porphyrin. The free-base porphyrin core is sufficiently electron-deficient that the hyperpolarizability does not increase on addition of a pyridinium electron-acceptor.

Spectroscopic studies of the mechanism of reversible photodegradation of 1-substituted aminoanthraquinone-doped polymers

“…Organic materials have a broad range of applications such as high-resolution fluorescence microscopy [1][2][3][4][5][6][7], second harmonic generation (SHG) microscopy [8][9][10][11][12], dye sensitized and polymer solar cells [13][14][15][16][17], solid state dye/organic lasers [18][19][20], and organic light emitting diodes [21,22], to name a few. Photostability of organic compounds and polymers is often a requirement for applications incorporating light-matter interaction [2-4, 6, 8, 18-20, 23-30].…”

Porphyrin Dyes for Nonlinear Optical Imaging of Live Cells

“…JW-1 and IG-1 dyes were functionalized with isophthalic derivatives substituted with four HEG and twelve TEG groups, respectively, instead of the pyridinium-based electron-acceptor group as the hydrophilic moiety. The dyes do not require pyridinium-based electron-acceptor groups because it has been previously shown that an acceptor group does not substantially contribute toward the nonlinear optical properties of free-base donor-acceptor-substituted porphyrin dyes ( Annoni et al., 2005 , Lopez-Duarte et al., 2013 , Morotti et al., 2006 ). Multiple HEG and TEG groups were used to enhance the aqueous solubility and amphiphilicity of dyes for efficient plasma membrane localization.…”

“…Until now, there has been only one report of an SHG-only dye (named as Ap3 ) that is suitable for multimodal imaging ( Nuriya et al., 2016 ). Although Ap3 possesses negligible fluorescence quantum yield and does not emit any fluorescence even in the far-red region unlike AK-1 , it generates similar or less SHG signals even than FM4-64 in contrast to the donor-acceptor porphyrin-based AK-1 , which gives almost three times more SHG signal than FM4-64 ( Khadria et al., 2017 , Lopez-Duarte et al., 2013 , Nuriya et al., 2016 , Reeve et al., 2009 ). Although AK-1 gives a fluorescence signal in the far-red to NIR regions even with a low fluorescence quantum yield, it does not give any fluorescence in the green and red regions, where most of the commercial cell markers emit ( Bestvater et al., 2002 ).…”

Porphyrins functionalized by quaternary pyridinium units

“…Porphyrins functionalized on meso-positions by quaternary pyridinium units, also referred to as cationic porphyrins are a large class of compounds with interesting physicochemical properties [22][23][24][25][26][27]. They serve as photosensitizers in photodynamic therapy (PDT) in treatment of cancer [28] and show affinity for serum albumin [29], important in drug delivery.…”