MDPI - Publisher of Open Access Journals

14 pages, 10738 KiB

Open AccessArticle

Effect of Chalcogenophenes on Chiroptical Activity of Twisted Tetracenes: Computational Analysis, Synthesis and Crystal Structure Thereof

by Gayathri Jothish Kumar, Benny Bogoslavsky, Sashi Debnath and Anjan Bedi

Molecules 2023, 28(13), 5074; https://doi.org/10.3390/molecules28135074 - 28 Jun 2023

Cited by 3 | Viewed by 2036

Abstract

The synthesis of multiply substituted acenes is still a relevant research problem, considering their applications and future potential. Here we present an elegant synthetic protocol to afford tetra-peri-substituted naphthalene and tetracene from their tetrahalo derivatives by a Pd(0)-catalyzed C-C cross-coupling method in a single step. The newly synthesized tetracenes were characterized by NMR, HRMS, UV-vis spectrophotometry, and single-crystal X-ray diffraction (SCXRD). In addition, the first systematic computational study of the effect of chalcogenophenyl substitutions on the chiroptical properties of twistacenes was reported here. The gas phase computational studies using density functional theory (DFT) on a series of chalcogenophene-substituted tetracenes revealed that their chiroptical activity could be systematically increased via the atomistic tuning of peripheral substituents. Full article

(This article belongs to the Section Organic Chemistry)

► Show Figures

Figure 1

12 pages, 3985 KiB

Open AccessArticle

Enhanced Ultrafast Broadband Reverse Saturable Absorption in Twistacenes with Enlarged π-Conjugated Central Bridge

by Xindi Liu, Wenfa Zhou, Mengyi Wang, Xingzhi Wu, Jidong Jia, Jinchong Xiao, Junyi Yang and Yinglin Song

Molecules 2022, 27(24), 9059; https://doi.org/10.3390/molecules27249059 - 19 Dec 2022

Cited by 2 | Viewed by 2100

Abstract

Optical nonlinearities of two all-carbon twistacenes, DPyA and DPyN, with the different π-conjugated central bridges were investigated. The nonlinear absorption properties of these compounds were measured using the femtosecond Z-scan with wavelengths between 650 and 900 nm. It has been found that the nonlinear absorption originated from two-photon absorption (TPA) and TPA-induced excited state absorption (ESA), wherein DPyA demonstrates higher performance than DPyN. The TPA cross section of DPyA (4300 GM) is nearly 4.3 times larger than that of DPyN at 650 nm. Moreover, the different central structures modulate the intensity of ESA at 532 nm, and DPyA exhibits an excellent ESA at 532 nm with multi-pulse excitation. Meanwhile, the result of data fitting and quantum chemistry calculation shows that the enhancement of nonlinear absorption in DPyA is due to the extended π- conjugated bridge and improved delocalization of π-electrons. These all-carbon twistacenes could yield potential applications in optical power limiting (OPL) technology. Full article

(This article belongs to the Topic Recent Advances in Nonlinear Optics and Nonlinear Optical Materials)
(This article belongs to the Section Materials Chemistry)

► Show Figures

Figure 1

12 pages, 2344 KiB

Open AccessArticle

Synthesis and Ultrafast Broadband Optical Limiting Properties of a Two-Branched Twistacene

by Yanbing Han, Jinchong Xiao, Xingzhi Wu, Yuxiao Wang, Xueru Zhang and Yinglin Song

Molecules 2022, 27(11), 3564; https://doi.org/10.3390/molecules27113564 - 1 Jun 2022

Cited by 9 | Viewed by 2001

Abstract

A novel two-branched twistacene (PyDN) has been designed and synthesized for application on ultrafast optical limiting. This twistacene exhibits excellent two photon absorption and two photon absorption-induced excited singlet state absorption, which was systematically investigated with a femtosecond Z-scan experiment, transient absorption spectrum, and two-photon excited fluorescence experiments. The admirable two photon absorption is attributed to the high degree of π electron delocalization in twistacene which is caused by introduction of two strong donors. The excited singlet state absorption cooperates with two-photon absorption to provide an excellent ultrafast optical limiting behavior with high linear transmittance, where the thresholds are 2.3–5.3 mJ/cm² in the spectral region of 532–800 nm of femtosecond laser and 133 mJ/cm² for picosecond pulse at 532 nm. These thresholds are lower than that of most of the optical limiters reported previously, which indicates PyDN is a promising candidate for ultrafast optical limiting. Full article

(This article belongs to the Topic Recent Advances in Nonlinear Optics and Nonlinear Optical Materials)
(This article belongs to the Section Materials Chemistry)

► Show Figures

Figure 1

Search Results (3)

Further Information

Guidelines

MDPI Initiatives

Follow MDPI

Saved Queries

Search Filter Reset All

Years

Feature Papers

Subjects

Journals

Article Types

Countries / Regions

Search Results (3)

Further Information

Guidelines

MDPI Initiatives

Follow MDPI