State of the Art of Boron and Tin Complexes in Second- and Third-Order Nonlinear Optics §

Abstract

Boron and tin complexes have been a versatile and very interesting scaffold for the design of nonlinear optical (NLO) chromophores. In this paper we present a wide range of reports since the 1990s to date, which include second-order (e.g., second harmonic generation) and third-order (e.g., two-photon absorption) NLO properties. After a short introduction on the origin of the NLO response in molecules, the different features associated with the introduction of these inorganic motifs in the organic-based NLO materials are discussed: Their effect on the accepting/donating capabilities of the substituents, on the efficiency of the π-conjugated linkage, and on the topology of the chromophores which can be tuned from the first generation of “push-pull” chromophores to more sophisticated two- or three-dimensional architectures.

Bithiophene‐Cored,mono‐,bis‐, andtris‐(Trimethylammonium)‐Substituted,bis‐Triarylborane Chromophores: Effect of the Number and Position of Charges on Cell Imaging and DNA/RNA Sensing

“…Three‐coordinate boron compounds have an empty p‐orbital at the boron center. Hence, such compounds are good π‐acceptors and display interesting photophysical and electrochemical properties, which lead to many different applications,[ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ] e. g., optoelectronics,[ 9 , 10 , 11 ] sensors for anions or small molecules,[ 12 , 13 , 14 , 15 , 16 , 17 ] and cell‐imaging agents and biomolecule sensors. [ 15 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ] For the latter applications, which were summarized very recently by Berger and Marder, [34] focusing on triarylboranes, water‐stable and soluble compounds are required.…”

Tuning the π-bridge of quadrupolar triarylborane chromophores for one- and two-photon excited fluorescence imaging of lysosomes in live cells

“…Furthermore, the electron deficiency of BAr 3 acceptor units make them especially useful in intramolecular charge transfer compounds, when conjugated to a π-donor (D) moiety 38–46. As excitation induced charge transfer properties increase the two-photon absorption (TPA) probability, triarylborane acceptors have great potential for use in TPA and for two-photon excited fluorescence (TPEF) 47,48…”

Synthetic Approaches to Triarylboranes from 1885 to 2020

“…Within the last few decades, compounds containing three-coordinate boron motifs have found increasing applicabilityi n variousfields including optoelectronics, [1][2][3] selective sensors for anions [4][5][6] or small molecules, [7,8] and bioimaging agents [9][10][11][12][13][14][15] due to the empty p-orbital att he boron center.W hereasn umerous compounds and their potentiala pplications have been reviewed by several groups, [16][17][18][19][20][21][22][23] synthetic methodology for the preparation of triarylboranes has been reviewed only rarely.In1 956, as ummary by Lappert et al gave avery general overview of the syntheses of many different types of organoboron compounds. [24] Very recently,M elen and co-workers summarized synthetic pathways to halogenated triarylboranes as well as their use in catalysis and frustrated Lewisp air (FLP) chemistry.…”

“…Within the last few decades, compounds containing three‐coordinate boron motifs have found increasing applicability in various fields including optoelectronics, [1–3] selective sensors for anions [4–6] or small molecules, [7, 8] and bioimaging agents [9–15] due to the empty p‐orbital at the boron center. Whereas numerous compounds and their potential applications have been reviewed by several groups, [16–23] synthetic methodology for the preparation of triarylboranes has been reviewed only rarely. In 1956, a summary by Lappert et al.…”