Modulated photophysics and photodynamics of ESIPT active molecule 1-(1H-benzo[d]imidazol-2-yl)naphthalen-2-ol inside cucurbit[7]uril nanocavity: a spectroscopic and quantum chemical approach

IF 1.6 4区化学 Q2 Agricultural and Biological Sciences

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2025-04-05 DOI:10.1007/s10847-025-01299-9

Akash Das, Anup Pramanik, Nikhil Guchhait

{"title":"Modulated photophysics and photodynamics of ESIPT active molecule 1-(1H-benzo[d]imidazol-2-yl)naphthalen-2-ol inside cucurbit[7]uril nanocavity: a spectroscopic and quantum chemical approach","authors":"Akash Das, Anup Pramanik, Nikhil Guchhait","doi":"10.1007/s10847-025-01299-9","DOIUrl":null,"url":null,"abstract":"<div>In this article, we have studied the modulated photophysics and photodynamic of an excited state proton transfer (ESIPT) molecule1-(1H-benzo[d]imidazol-2-yl)naphthalen-2-ol (H-BINO) following host-guest inclusion complexation with water-soluble host Cucurbit[7]uril (CB7) with the help of steady-state, time-resolved spectroscopic measurements and is supported by Density Functional Theory (DFT) calculations. The change of absorbance and fluorescence enhancement with blue shift of emission maxima indicates host-guest inclusion complexation and favourable enol-keto photo-isomerisation of H-BINO inside the CB7 nanocavity. Complexation offers an increment of excited state lifetime from 0.7ns and 2.1ns observed in aqueous medium to 0.8 ns and 3.3 ns in CB7 cavity due to structural rigidity and thereby minimizing non-radiative processes. Benesi-Hildebrand (BH) plot indicates the formation of 1:1 inclusion complex (H-BINO: CB7) which is supported by time-resolved anisotropy measurement. Solvation of H-BINO inside the CB7 cavity is faster at the beginning and slows down over time with solvation correlation time of 2.46 ns. Computational structural calculations at DFT level support that inside the CB7 cavity, the reversal of stability of proton transfer keto-form with respect to the enol-form in the first excited state than the ground state. Blue shifting of experimental absorption and emission maxima inside CB7 nanocavityis well correlate with DFT calculated bands.</div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"105 7-8","pages":"463 - 473"},"PeriodicalIF":1.6000,"publicationDate":"2025-04-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10847-025-01299-9","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Agricultural and Biological Sciences","Score":null,"Total":0}

引用次数: 0

Abstract

In this article, we have studied the modulated photophysics and photodynamic of an excited state proton transfer (ESIPT) molecule1-(1H-benzo[d]imidazol-2-yl)naphthalen-2-ol (H-BINO) following host-guest inclusion complexation with water-soluble host Cucurbit[7]uril (CB7) with the help of steady-state, time-resolved spectroscopic measurements and is supported by Density Functional Theory (DFT) calculations. The change of absorbance and fluorescence enhancement with blue shift of emission maxima indicates host-guest inclusion complexation and favourable enol-keto photo-isomerisation of H-BINO inside the CB7 nanocavity. Complexation offers an increment of excited state lifetime from 0.7ns and 2.1ns observed in aqueous medium to 0.8 ns and 3.3 ns in CB7 cavity due to structural rigidity and thereby minimizing non-radiative processes. Benesi-Hildebrand (BH) plot indicates the formation of 1:1 inclusion complex (H-BINO: CB7) which is supported by time-resolved anisotropy measurement. Solvation of H-BINO inside the CB7 cavity is faster at the beginning and slows down over time with solvation correlation time of 2.46 ns. Computational structural calculations at DFT level support that inside the CB7 cavity, the reversal of stability of proton transfer keto-form with respect to the enol-form in the first excited state than the ground state. Blue shifting of experimental absorption and emission maxima inside CB7 nanocavityis well correlate with DFT calculated bands.

查看原文本刊更多论文

ESIPT活性分子1-（1h -苯并[d]咪唑-2-基）萘-2-醇在瓜bbbbl纳米腔中的调制光物理和光动力学：光谱和量子化学方法

在本文中，我们研究了激发态质子转移（ESIPT）分子1-（1h -苯并[d]咪唑-2-酰基）萘-2-醇（H-BINO）与水溶性宿主Cucurbit b[7]uril （CB7）的主客体包合后的调制光物理和光动力学，并利用稳态、时间分辨率光谱测量和密度泛函理论（DFT）计算支持。吸光度和荧光增强随发射最大值蓝移的变化表明，在CB7纳米腔内，H-BINO发生了主客体包合和烯醇-酮-光异构化。由于结构刚性，络合使激发态寿命从水介质中的0.7ns和2.1ns增加到CB7腔中的0.8 ns和3.3 ns，从而最大限度地减少了非辐射过程。Benesi-Hildebrand （BH）图表明，时间分辨各向异性测量支持了1:1包合物（H-BINO: CB7）的形成。H-BINO在CB7空腔内的溶剂化开始较快，随着时间的推移逐渐减慢，溶剂化相关时间为2.46 ns。在DFT水平上的计算结构计算支持了CB7腔内，质子转移酮型相对于烯醇型的稳定性在第一激发态比基态的逆转。CB7纳米腔内实验吸收和发射最大值的蓝移与DFT计算波段有很好的相关性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Journal of Inclusion Phenomena and Macrocyclic Chemistry 化学-化学综合

CiteScore

3.30

自引率

8.70%

发文量

审稿时长

3-8 weeks

期刊介绍： The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.