Large-Scale Virtual Design and Scaffold Diversity Analysis of Triphenylamine Organic Dyes Through Fragment-Based Enumeration and Network-Centric Chemical Space Exploration.

Rational design of functional organic dyes is vital in the development of optoelectronics and bioimaging fields, in which structural variety and synthesis feasibility should be considered. In this study, a holistic computational approach to investigate the chemical space of triphenylamine-derived chromophores is proposed by using similarity-based analysis, synthetic accessibility assessment, and fragmentation-based molecule generation methods. Through employing the BRICS algorithm, more than 10,000 new molecules were designed. The structural relationships among generated molecules were studied based on similarity score calculation, cluster formation, and visualization in the chemical space network. The selected standard molecules have shown good absorption properties and easy-to-use synthesis processes. Comparing the structural characteristics of three representative dyes (H1, H2, and H4), three different kinds of scaffolds can be recognized.