Design, synthesis and photobiological activity of novel ruthenium phthalocyanine complexes

Synthesis of a Naphthalocyanine-Like Dye: The First Report on Zn(II)-1,6-methano[10]annulenecyanine

“…The synthesis of the building block 3,4-dicyano-1,6-methano [10]annulene (9) was carried out as shown in Scheme 1 [35]. First, cycloheptatriene (1) was mono-acetylated at low temperature by a Friedel-Crafts reaction furnishing compound 2 in 60% yield.…”

“…Near-infrared (NIR) dyes have received increasing attention due to their versatile applications in materials science [1][2][3][4][5], medical applications [6][7][8][9][10][11][12][13][14], catalysis and other advanced technology devices [12,[15][16][17]. In this context, phthalocyanines and naphthalocyanines are very robust dyes with relevant photophysical properties and must be highlighted [18][19][20][21][22][23].…”

“…Seeking for new NIR building blocks our group decided to explore a class of molecules called 1,x-methano [10]annulenes, especially the 1,6-methano [10]annulene ( Figure 1) [32]. These compounds have fascinated a number of scientists since Emanuel Vogel's discovery in 1964 [33].…”

“…These compounds have fascinated a number of scientists since Emanuel Vogel's discovery in 1964 [33]. Vogel and coworkers achieved the required planarity of fully conjugated 10-membered carbon rings by inserting a carbon bridge between C-1 and C-6 ( Figure 1), thus furnishing 1,6-methano [10]annulene as an example of an aromatic cyclodecapentaene ring. Up to now, this class of compounds was extensively studied in synthetic, theoretical and biological areas [34].…”

“…suitable derivatives of these compounds have not been described in the literature as building blocks for phthalocyanine and naphthalocyanine-like compounds. Herein, we describe two approaches for the synthesis of a new naphthalocyanine-like compound which we name as Zn(II)-1,6-methano [10]annulenecyanine (10), using annulenenitrile 9 and annulenemaleimide 13 as building blocks (Schemes 1-5).…”