Synthesis and Optical Property Modulation of Substituted [2,2]-paracylophanes through Through-Space Conjugation

21 November 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

4,16-para-substituted [2,2] paracylophane with naphthalene (PCP-NAP), anthracene (PCP-ANTH), and tetraphenylethylene (PCP-TPE) as a new through-space conjugated dimers were prepared by the Suzuki–Miyaura cross-coupling reaction of 4,16-diboryl [2,2] paracyclophane and respective bromo derivative using Pd(PPh3)4 as a catalyst and KOH as a base. The synthesized compounds were fully characterized by NMR, HR-MS and their photophysical, and electrochemical properties were studied. The quantum yield of PCP-NAP and PCP-ANTH were calculated and estimated as 0.21 and 0.50. PCP-TPE exhibited aggregation-induced emission characteristics when the water fraction was higher than 40% in the THF/water mixtures, it crystallizes in the centrosymmetric triclinic space group P⎼1 with one molecule residing on the inversion centre. The observed properties of these π-stacked dimers were compared to conjugation length in the structure.

Keywords

Suzuki–Miyaura cross-coupling reaction
Aggregation Induced Emission
Space Conjugation
[2.2] paracylophane

Supplementary materials

Title
Description
Actions
Title
Synthesis and Optical Property Modulation of Substituted [2,2]-paracylophanes through Through-Space Conjugation
Description
The supplementary material includes NMR plots, Mass Spectra and other analytical data for all the newly synthesized molecules. It also includes the crystallographic data for the compound 5.
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.