Synthesis and the spectral, electrochemical, and nonlinear optical properties of β-dicyanovinyl-appended ‘push–pull’ porphyrins

Abstract

A series of “push-pull” porphyrins, MTPP(MN)(TPA)2 (M = 2H, CuII, NiII, and ZnII) having triphenylamine (TPA) and dicyanovinyl (DCN) at antipodal positions were synthesized and characterised by UV-Vis, fluorescence and...

Theoretical designing of non-fullerene derived organic heterocyclic compounds with enhanced nonlinear optical amplitude: a DFT based prediction

“…The two-photon absorption coefficients ( β ) are found in the range of 0.87 × 10 −13 to 4.28 × 10 −13 m W −1 while, the nonlinear refractive index ( n 2 ) in the range of 1.21 × 10 −19 to 7.36 × 10 −19 m 2 W −1 . The results revealed them as potential candidates in the nonlinear optics and photonic devices 22 . Keeping in view the above discussion, herein, we have taken BDTN-Th as a parent non-fullerene acceptor molecule 23 and modified it into a new reference compound ( TPBR1 ): 2-(( Z )-5-((6-((2-(( Z )-(4-(dicyanomethylene)-6-oxo-4 H -cyclopenta[c]thiophen-5(6 H )-ylidene)methyl)-4-isobutyl-4 H -thieno[3,2-b]pyrrol-6-yl)thiophen)-4-isobutyl-5,8-dimethoxy-4 H -benzo[4,5]thieno[3,2-b]thieno[2,3-d]pyrrol-2-yl)methylene)-6-oxo-5,6-dihydro-4 H -cyclopenta[c]thiophen-4-ylidene)malononitrile 23 .…”

Ethyl acetoacetate and acetylacetone appended hexabromo porphyrins: synthesis, spectral, electrochemical, and femtosecond third-order nonlinear optical studies

“…25 Porphyrins possessing nitro or cyano groups promote the reduction of the HOMO-LUMO gap as compared to their precursor, causing a bathochromic shift in the λ max in optical absorption spectra and also tunable redox properties. 29,30 The NLO behavior of a variety of porphyrins has been investigated by our group including push-pull meso-substituted trans-A 2 BC porphyrins, where A is mesityl, B is phenothiazine ( push) and C is an o/p-nitrophenyl moiety ( pull); 8 push-pull porphyrins containing TPA-CHO/NO 2 (TPA; triphenylamine) at antipodal positions; 10 highly electron-deficient TCBDappended porphyrins; 31 highly polarizable push-pull porphyrins containing TPA and DCN (dicyanovinyl) at the antipodal position; 32 and unsymmetrically β-functionalized porphyrins appended via nitro and methyl acrylate/mono-benzo groups. 33 To date, non-planar electron-deficient hexa-bromo porphyrins bearing one acac/EAA moiety at the β-position remain unexplored towards NLO applications.…”

Theoretical study on porphyrin arch-tapes of carbonyl-inserted seven-membered rings with high nonlinear optical properties

“…In addition, the optical, electronic, and magnetic properties of porphyrins can be regulated by varying the inner core metal ions. 9,11 For example, alkali and transition metals doped directly in porphyrins allow for significant modulation of their optical and electronic properties. Gao et al have designed and investigated a series of crown-porphyrin complexes (K@Cr-Pr, CrPr@Zn, and K@Cr-Pr@Zn) with the aid of alkali and transition metals by DFT calculations.…”